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Hangzhou Think Chemical Co. Ltd

Darunavir Ethanolate[CAS:635728-49-3] [(3R, 3aS, 6aR)-Hydroxyhexa hydrofuro [2, 3-è] furanyl Succin[CAS:253265-97-3] HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufac

Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate

Cas:253265-97-3

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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Kono Chem Co.,Ltd

CAS No.: 253265-97-3 Other Names: 253265-97-3 MF: C11H13NO7 EINECS No.: - Place of Origin: Shannxi, China (Mainland) Type: Pharmaceutical Intermediates, Synt

High quality Carbonic acid 2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Cas:253265-97-3

Min.Order:1 Kilogram

FOB Price: $450.0 / 500.0

Type:Other

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

We can provide GMP validation service that complies with SFDA, FDA, WHO and EU EMPA.Excellent registration team could help us easlily to register our products in different countries.If you and your customer are interested in some products or need CMO

Hebei yanxi chemical co.,LTD.

Hebei yanxi chemical co. LTD. has expanded a compositive entity from initially only as a small manufacturer. The company dedicated to the development, production and marketing of chemicals. After many years of efforts, we have established stable

Carbonic acid,2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Cas:253265-97-3

Min.Order:1 Metric Ton

FOB Price: $1.0 / 2.0

Type:Manufacturers

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Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Carbonic acid 2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Cas:253265-97-3

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Henan Tianfu Chemical Co., Ltd.

Competitive Price High Quality Fast Delivery custom-made Welcome to Henan Tianfu Chemical Co., Ltd. website. Our company engages in Sodium Tripolyphosphate (STPP) and Sodium Hexametabphosphate (SHMP) production; development of noble me

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate 253265-97-3

Cas:253265-97-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Jinan Finer Chemical Co., Ltd

Product Description Product name Carbonic acid 2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester CAS number 2

Carbonic acid 2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Cas:253265-97-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate

Cas:253265-97-3

Min.Order:1 Kilogram

FOB Price: $9.0 / 99.0

Type:Trading Company

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Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Pharmaceutical Grade CAS 253265-97-3 with competitive price

Cas:253265-97-3

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Henan Wentao Chemical Product Co., Ltd.

We are leading fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.Our main business covers the fields below: 1.Noble Metal Catalysts (Pt.Pd...) 2.Orga

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl CarbonateCAS NO.253265-97-3

Cas:253265-97-3

Min.Order:1 Kilogram

FOB Price: $5.0

Type:Lab/Research institutions

inquiry

Hubei Langyou International Trading Co., Ltd

Advantages: Hubei XinRunde Chemical Co., Ltd is a renowned pharmaceutical manufacturer. We can offer high quality products at competitive price in quick delivery with 100% custom pass guaranteed. Never stop striving to offer our best s

Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

Carbonic acid,2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester 253265-97-3

Cas:253265-97-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At present,

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate WITH CAS:253265-97-3

Cas:253265-97-3

Min.Order:1 Kilogram

FOB Price: $1400.0

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate CAS: 253265-97-3 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemica

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate CAS: 253265-97-3

Cas:253265-97-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Carbonic acid,2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Cas:253265-97-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Triumph International Development Limilted

Appearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:By

(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanylSuccinimidylCarbonate(SM9)

Cas:253265-97-3

Min.Order:100 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Keyingchem Co.,Ltd

Hangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate

Cas:253265-97-3

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments

CARBONIC ACID 2,5-DIOXO-1-PYRROLIDINYL [(3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL] ESTER

Cas:253265-97-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Maytime Bio-Tech Co.,Ltd.

We are supplying below Darunavir Intermediate with good quality and competitive price. (3aS,4S,6aR)-Tetrahydro-4-methoxy-furo[3,4-b]furan-2(3H)-one CAS No 866594-60-7 4-Amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)

Darunavir intermediate CAS:253265-97-3

Cas:253265-97-3

Min.Order:10 Gram

Negotiable

Type:Other

inquiry

Saiwante (shanghai) New Material Technology Co., Ltd.

Vapor Pressure:2.41E-06mmHg at 25°C Melting Point:122-125℃ Refractive Index:1.562 Boiling Point:391.8 °C at 760 mmHg Flash Point:190.7 °C PSA:91.37000 Density:1.51 g/cm3 LogP:-0.09710 Storage Temp.:2-8°C Solubility

253265-97-3 2,5-Dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate

Cas:253265-97-3

Min.Order:1 Gram

FOB Price: $6.0

Type:Trading Company

inquiry

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

Carbonic acid,2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Cas:253265-97-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

HANWAYS CHEMPHARM CO.,LIMITED

We are concentrating on APIs and pharmaceutical intermediates. It is made obtainable from us at the most reasonable rate. Appearance:White powder Storage:Store at +4°C Package:25KG/DRUM Application:Blood lipid regulation, anti - atherosclerosis d

Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

High quality Carbonic acid 2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Cas:253265-97-3

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

SHANGHAI SYSTEAM BIOCHEM CO., LTD

We are one of a few suppliers that can offer custom synthesis service of this product We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to prov

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate

Cas:253265-97-3

Min.Order:100 Gram

FOB Price: $100.0 / 2000.0

Type:Lab/Research institutions

inquiry

HANGZHOU YUNUO CHEMICAL CO.,LTD

Superior quality, moderate price & quick delivery. Appearance:white powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:25kg/drum, or as per your request. Application:Used as Pharmaceutical Intermediates Tr

Carbonic acid,2,5-dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Cas:253265-97-3

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Siwei Development Group Ltd.

Product name: 1-({[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}oxy)pyrrolidine-2,5-dione CAS No.:253265-97-3 Molecule Formula:C11H13NO7 Molecule Weight:271.22 Purity: 98.0% Package: 25kg/drum Description:White to off-white p

Zibo Dorne chemical technology co. LTD

Product Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate

Cas:253265-97-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

C7H9ClO4

C7H9ClO4

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 2h; Reflux;99.6%
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
156928-09-5

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
With pyridine In tert-butyl methyl ether at 25 - 40℃; for 62h; Solvent;90%
With triethylamine In acetonitrile at 23℃; for 7h;66%
With triethylamine In dichloromethane Solvent; Reagent/catalyst; Inert atmosphere; Reflux; Large scale;62%
γ-benzyloxymethyl-α,β-butenolide
72605-53-9

γ-benzyloxymethyl-α,β-butenolide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: benzophenone / 9 h / 0 °C / UV-irradiation
2: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C
3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
5: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C
6: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C
7: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
Multi-step reaction with 7 steps
1: benzophenone / 9 h / 0 °C / UV-irradiation
2: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C
3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
5: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C
6: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C
7: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
(5S)-5-(hydroxymethyl)-5H-furan-2-one
78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: benzophenone / 4 h / 0 °C / UV-irradiation
2: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
3: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
4: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C
5: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C
6: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
Multi-step reaction with 6 steps
1: benzophenone / 4 h / 0 °C / UV-irradiation
2: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
3: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
4: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C
5: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C
6: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate
81703-94-8

methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 97 percent / H2SO4 / methanol / 2 h / 23 °C
2: benzophenone / 4 h / 0 °C / UV-irradiation
3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
5: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C
6: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C
7: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
Multi-step reaction with 7 steps
1: 97 percent / H2SO4 / methanol / 2 h / 23 °C
2: benzophenone / 4 h / 0 °C / UV-irradiation
3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
5: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C
6: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C
7: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
(4S,5S)-4-(1,3-dioxolan-2-yl)-5-hydroxymethyldihydrofuran-2-one
140156-47-4

(4S,5S)-4-(1,3-dioxolan-2-yl)-5-hydroxymethyldihydrofuran-2-one

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
2: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
3: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C
4: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C
5: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
Multi-step reaction with 5 steps
1: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
2: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
3: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C
4: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C
5: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate
186488-54-0

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C
2: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
(3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one
809286-93-9

(3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C
2: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
(3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan
252873-50-0

(3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C
2: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C
3: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
Multi-step reaction with 3 steps
1: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C
2: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C
3: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
(S)-1-(benzyloxy)but-3-en-2-yl acrylate
681463-02-5

(S)-1-(benzyloxy)but-3-en-2-yl acrylate

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 98 percent / second generation Grubb's catalyst / CH2Cl2 / 5 h / Heating
2: benzophenone / 9 h / 0 °C / UV-irradiation
3: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C
4: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
5: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
6: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C
7: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C
8: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
Multi-step reaction with 8 steps
1: 98 percent / second generation Grubb's catalyst / CH2Cl2 / 5 h / Heating
2: benzophenone / 9 h / 0 °C / UV-irradiation
3: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C
4: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
5: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
6: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C
7: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C
8: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
(2S,53)-3-(1,3-dioxolan-2-yl)pentane-1,2,5-triol
681463-04-7

(2S,53)-3-(1,3-dioxolan-2-yl)pentane-1,2,5-triol

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
2: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C
3: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C
4: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
Multi-step reaction with 4 steps
1: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
2: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C
3: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C
4: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
(4S,5S)-5-(benzyloxymethyl)-4-(1,3-dioxolan-2-yl)dihydrofuran-2-one
681463-03-6

(4S,5S)-5-(benzyloxymethyl)-4-(1,3-dioxolan-2-yl)dihydrofuran-2-one

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C
2: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
3: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
4: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C
5: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C
6: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
Multi-step reaction with 6 steps
1: 89 percent / H2 / Pd/C / methanol / 24 h / 23 °C
2: LiAlH4 / tetrahydrofuran / 4 h / 0 °C
3: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3
4: 94 percent / 4-methylmorpholino-N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 0.17 h / 23 °C
5: 70 percent / NaBH4 / ethanol / 2.5 h / -18 °C
6: 66 percent / Et3N / acetonitrile / 7 h / 23 °C
View Scheme
vinyl acetate
108-05-4

vinyl acetate

di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

(3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
109789-19-7

(3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

A

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

B

(3S,3aS,6aR)-perhydrofuro[2,3-b]furan-3-yl acetate

(3S,3aS,6aR)-perhydrofuro[2,3-b]furan-3-yl acetate

Conditions
ConditionsYield
Stage #1: vinyl acetate; (3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol In dichloromethane; tert-butyl methyl ether at 20℃; for 5h; Resolution of racemate; Large scale reaction; Enzymatic reaction;
Stage #2: di(succinimido) carbonate With triethylamine In acetonitrile at 20℃; for 24h; enantioselective reaction;
A 5.1 g
B n/a
3,4-dihydroxy-2-(2-hydroxyethyl)butanal

3,4-dihydroxy-2-(2-hydroxyethyl)butanal

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride / water / 20 h / 2 - 5 °C
1.2: 1 h
2.1: triethylamine / acetonitrile / 5 h / 20 °C / Inert atmosphere
View Scheme
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

(3S,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

(3S,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
With triethylamine In acetonitrile at 24 - 45℃; for 1h;
(3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<2,3-b>furan

(3SR,3aRS,6aSR)-3-hydroxy-4H-hexahydrofuro<2,3-b>furan

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Lipase PS / 24 h / 50 °C / Enzymatic reaction
2: triethylamine / acetonitrile / 24 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: lipase AS / 24 h / 50 °C / Enzymatic reaction
2: triethylamine / acetonitrile / 24 h / 20 °C / Inert atmosphere
View Scheme
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
156928-09-5

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 3 h / 50 °C
2: triethylamine / tetrahydrofuran / 2 h / Reflux
View Scheme
hexahydrofuro[2,3-b]furan-3-ol
109789-19-7

hexahydrofuro[2,3-b]furan-3-ol

di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
With pyridine In toluene at 40℃; for 9h;71.9 g
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 25 h / 0 - 30 °C
2.1: sodium tetrahydroborate; lithium bromide / tetrahydrofuran / 35 h / 0 - 30 °C
2.2: 0.33 h / 25 - 30 °C / Inert atmosphere
2.3: 5 h / 0 - 30 °C / Inert atmosphere
3.1: pyridine / dichloromethane / 17 h / 40 - 45 °C
View Scheme
Multi-step reaction with 4 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 25 h / 0 - 30 °C
2: lithium bromide; lithium borohydride / tetrahydrofuran / 18 h / 0 - 30 °C / Inert atmosphere
3: sulfuric acid; sodium hydroxide / water / 2 h / 5 - 30 °C
4: pyridine / dichloromethane / 17 h / 40 - 45 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 25 h / 0 - 30 °C
2.1: methanol; hydrogenchloride / 3 h / 25 - 30 °C
3.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 3 h / 65 - 70 °C
4.1: potassium tert-butylate / methanol / 0.17 h / 25 - 30 °C
4.2: 3 h / 0 - 30 °C
5.1: pyridine / dichloromethane / 17 h / 40 - 45 °C
View Scheme
ethyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-nitrobutanoate

ethyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-nitrobutanoate

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate; lithium bromide / tetrahydrofuran / 35 h / 0 - 30 °C
1.2: 0.33 h / 25 - 30 °C / Inert atmosphere
1.3: 5 h / 0 - 30 °C / Inert atmosphere
2.1: pyridine / dichloromethane / 17 h / 40 - 45 °C
View Scheme
Multi-step reaction with 3 steps
1: lithium bromide; lithium borohydride / tetrahydrofuran / 18 h / 0 - 30 °C / Inert atmosphere
2: sulfuric acid; sodium hydroxide / water / 2 h / 5 - 30 °C
3: pyridine / dichloromethane / 17 h / 40 - 45 °C
View Scheme
Multi-step reaction with 4 steps
1.1: methanol; hydrogenchloride / 3 h / 25 - 30 °C
2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 3 h / 65 - 70 °C
3.1: potassium tert-butylate / methanol / 0.17 h / 25 - 30 °C
3.2: 3 h / 0 - 30 °C
4.1: pyridine / dichloromethane / 17 h / 40 - 45 °C
View Scheme
(S)-5-Hydroxymethyl-4-nitromethyl-dihydro-furan-2-one

(S)-5-Hydroxymethyl-4-nitromethyl-dihydro-furan-2-one

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 3 h / 65 - 70 °C
2.1: potassium tert-butylate / methanol / 0.17 h / 25 - 30 °C
2.2: 3 h / 0 - 30 °C
3.1: pyridine / dichloromethane / 17 h / 40 - 45 °C
View Scheme
C6H13NO5

C6H13NO5

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / methanol / 0.17 h / 25 - 30 °C
1.2: 3 h / 0 - 30 °C
2.1: pyridine / dichloromethane / 17 h / 40 - 45 °C
View Scheme
3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-nitrobutan-1-ol

3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-nitrobutan-1-ol

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; sodium hydroxide / water / 2 h / 5 - 30 °C
2: pyridine / dichloromethane / 17 h / 40 - 45 °C
View Scheme
ethyl 2-((3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)acetate
59256-86-9

ethyl 2-((3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)acetate

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: sodium periodate / methanol / 2 h / 0 - 23 °C
2.1: sodium tetrahydroborate / methanol / 1 h / 0 °C
3.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere
4.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
4.2: 6 h / -78 - 23 °C
5.1: potassium carbonate / methanol / 0.25 h / 0 °C
6.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
8.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
9.2: 1.5 h / 0 °C
9.3: 1 h / 0 - 23 °C
10.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme
ethyl 2-[(3aR,5S,6R,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl]acetate
178557-39-6

ethyl 2-[(3aR,5S,6R,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl]acetate

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
2.2: 6 h / -78 - 23 °C
3.1: potassium carbonate / methanol / 0.25 h / 0 °C
4.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
6.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
7.2: 1.5 h / 0 °C
7.3: 1 h / 0 - 23 °C
8.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme
(3aS,4S,6aR)-2-Oxo-hexahydro-furo[3,4-b]furan-4-carbaldehyde
58399-68-1

(3aS,4S,6aR)-2-Oxo-hexahydro-furo[3,4-b]furan-4-carbaldehyde

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
2.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
3.2: 1.5 h / 0 °C
3.3: 1 h / 0 - 23 °C
4.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme
(Z)-ethyl 2-((3aR,5S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethylfuro[2,3-d][1,3]dioxol-6(3aH,5H,6aH)-ylidene)acetate
57466-98-5

(Z)-ethyl 2-((3aR,5S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethylfuro[2,3-d][1,3]dioxol-6(3aH,5H,6aH)-ylidene)acetate

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: water; acetic acid / 60 h / 23 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
2.2: 6 h / -78 - 23 °C
3.1: potassium carbonate / methanol / 0.25 h / 0 °C
4.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
6.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
7.2: 1.5 h / 0 °C
7.3: 1 h / 0 - 23 °C
8.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme
(Z)-ethyl 2-((3aR,5S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ylidene)acetate
950583-17-2

(Z)-ethyl 2-((3aR,5S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ylidene)acetate

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: palladium 10% on activated carbon; hydrogen / ethanol / 24 h / 760.05 Torr
2.1: sodium periodate / methanol / 2 h / 0 - 23 °C
3.1: sodium tetrahydroborate / methanol / 1 h / 0 °C
4.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere
5.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
5.2: 6 h / -78 - 23 °C
6.1: potassium carbonate / methanol / 0.25 h / 0 °C
7.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
9.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
10.2: 1.5 h / 0 °C
10.3: 1 h / 0 - 23 °C
11.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme
3-deoxy-3-(2-ethoxy-2-oxoethyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose
1008743-57-4

3-deoxy-3-(2-ethoxy-2-oxoethyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / methanol / 1 h / 0 °C
2.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere
3.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
3.2: 6 h / -78 - 23 °C
4.1: potassium carbonate / methanol / 0.25 h / 0 °C
5.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
7.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
8.2: 1.5 h / 0 °C
8.3: 1 h / 0 - 23 °C
9.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme
((3aR,5R,6aS)-2,2-dimethyl-6-oxotetrahydrofuro[2,3-d][1,3]-dioxol-5-yl)methyl benzoate

((3aR,5R,6aS)-2,2-dimethyl-6-oxotetrahydrofuro[2,3-d][1,3]-dioxol-5-yl)methyl benzoate

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: palladium 10% on activated carbon; hydrogen / ethanol / 6 h / 23 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
2.2: 6 h / -78 - 23 °C
3.1: potassium carbonate / methanol / 0.25 h / 0 °C
4.1: disodium hydrogenphosphate; Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C
6.1: hydrogenchloride / methanol / 12 h / 0 - 23 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere
7.2: 1.5 h / 0 °C
7.3: 1 h / 0 - 23 °C
8.1: triethylamine / acetonitrile / 16 h / 23 °C / Inert atmosphere
View Scheme
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane
156732-15-9

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 24h;100%
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride
251105-80-3

N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-{(1S,2R)-2-hydroxy-3-[(2-methylpropyl)-4-nitrophenylsulfonylamino]-1-phenylmethylpropyl}carbamate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-{(1S,2R)-2-hydroxy-3-[(2-methylpropyl)-4-nitrophenylsulfonylamino]-1-phenylmethylpropyl}carbamate

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 6h;98.9%
With triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;95%
With triethylamine In dichloromethane
1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-amine

1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-amine

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

[(2R,3S)-3-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]amino]-2-hydroxy-4-phenylbutyl](2-methylpropyl)carbamic acid phenylmethyl ester
865105-52-8

[(2R,3S)-3-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]amino]-2-hydroxy-4-phenylbutyl](2-methylpropyl)carbamic acid phenylmethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 24h;96.4%
With N-ethyl-N,N-diisopropylamine In dichloromethane
With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Inert atmosphere;5.8 g
1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride

1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

[(2R,3S)-3-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]amino]-2-hydroxy-4-phenylbutyl](2-methylpropyl)carbamic acid phenylmethyl ester
865105-52-8

[(2R,3S)-3-[[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]amino]-2-hydroxy-4-phenylbutyl](2-methylpropyl)carbamic acid phenylmethyl ester

Conditions
ConditionsYield
Stage #1: 1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride; 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In dichloromethane at 20℃; for 24h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
96.4%
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide
169280-56-2

4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide

darunavir

darunavir

Conditions
ConditionsYield
In dimethyl sulfoxide at 15 - 30℃; Solvent;94%
With triethylamine In dichloromethane at 20℃;90%
With potassium carbonate In Isopropyl acetate; water at 15 - 35℃; for 4h;83.33%
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate
159006-03-8

tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate

{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester
206362-00-7

{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions
ConditionsYield
Stage #1: tert-butyl (1S,2R)-1-benzyl-2-hydroxy-3-{isobutyl[(4-methoxyphenyl)sulfonyl]amino}propylcarbamate With trifluoroacetic acid In dichloromethane at 23℃; for 0.666667h;
Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In dichloromethane at 23℃; for 3h;
90%
N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)(2-methylbenzimidazol-5-yl)sulfonamide

N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)(2-methylbenzimidazol-5-yl)sulfonamide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

[(1S,2R)-2-hydroxy-3-[[(2-methylbenzimidazol-5-yl)sulfonyl](2-methylpropyl)amino]-1-(phenylmethyl)propyl]carbamic acid [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

[(1S,2R)-2-hydroxy-3-[[(2-methylbenzimidazol-5-yl)sulfonyl](2-methylpropyl)amino]-1-(phenylmethyl)propyl]carbamic acid [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 17h;89%
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane
183004-94-6

3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane

darunavir

darunavir

Conditions
ConditionsYield
Stage #1: 3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane With trifluoroacetic acid In dichloromethane at 23℃; for 0.666667h;
Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In dichloromethane at 23℃; for 3h;
89%
N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester
160233-05-6

N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

GRL-98065

GRL-98065

Conditions
ConditionsYield
Stage #1: N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In acetonitrile at 20℃; for 4h; Further stages.;
82%
Stage #1: N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In acetonitrile at 20℃; for 4h;
82%
C31H47BN2O7S

C31H47BN2O7S

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

C33H47BN2O9S

C33H47BN2O9S

Conditions
ConditionsYield
Stage #1: C31H47BN2O7S With hydrogenchloride In 1,4-dioxane for 4h;
Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In dichloromethane at 20℃; Inert atmosphere;
82%
C30H45BN2O7S

C30H45BN2O7S

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

C32H45BN2O9S

C32H45BN2O9S

Conditions
ConditionsYield
Stage #1: C30H45BN2O7S With hydrogenchloride In 1,4-dioxane at 22℃; under 760.051 Torr; for 4h; Inert atmosphere;
Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With triethylamine In dichloromethane at 22℃; under 760.051 Torr; for 16h; Inert atmosphere;
82%
N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-N-benzyl-4-methoxybenzenesulfonamide

N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-N-benzyl-4-methoxybenzenesulfonamide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-4-((N-benzyl-4-methoxyphenyl)-sulfonamido)-3-hydroxybutan-2-yl)carbamate

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-4-((N-benzyl-4-methoxyphenyl)-sulfonamido)-3-hydroxybutan-2-yl)carbamate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 48h;80%
2-Dimethylamino-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide
660410-38-8

2-Dimethylamino-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

{(1S,2R)-1-Benzyl-3-[(2-dimethylamino-benzothiazole-6-sulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

{(1S,2R)-1-Benzyl-3-[(2-dimethylamino-benzothiazole-6-sulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;78%
2-(2-Pyrrolidin-1-yl-ethylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide
473739-14-9

2-(2-Pyrrolidin-1-yl-ethylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

((1S,2R)-1-Benzyl-2-hydroxy-3-{isobutyl-[2-(2-pyrrolidin-1-yl-ethylamino)-benzothiazole-6-sulfonyl]-amino}-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

((1S,2R)-1-Benzyl-2-hydroxy-3-{isobutyl-[2-(2-pyrrolidin-1-yl-ethylamino)-benzothiazole-6-sulfonyl]-amino}-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;76%
N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-4-(1,3-dioxoisoindolin-2-yl)-N-isobutylbenzenesulfonamide

N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-4-(1,3-dioxoisoindolin-2-yl)-N-isobutylbenzenesulfonamide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2S,3R)-4-(4-(1,3-dioxoisoindolin-2-yl)-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2S,3R)-4-(4-(1,3-dioxoisoindolin-2-yl)-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate

Conditions
ConditionsYield
With triethylamine In water; ethyl acetate at 25 - 35℃;73.19%
2-[Methyl-(2-pyrrolidin-1-yl-ethyl)-amino]-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

2-[Methyl-(2-pyrrolidin-1-yl-ethyl)-amino]-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

[(1S,2R)-1-Benzyl-2-hydroxy-3-(isobutyl-{2-[methyl-(2-pyrrolidin-1-yl-ethyl)-amino]-benzothiazole-6-sulfonyl}-amino)-propyl]-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

[(1S,2R)-1-Benzyl-2-hydroxy-3-(isobutyl-{2-[methyl-(2-pyrrolidin-1-yl-ethyl)-amino]-benzothiazole-6-sulfonyl}-amino)-propyl]-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;73%
C35H38ClFN4O4
1311412-72-2

C35H38ClFN4O4

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

C42H46ClFN4O8
1311410-46-4

C42H46ClFN4O8

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 1h;73%
1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

{(1S,2R)-[1-(4-formyl-benzyl)]-(2R)-2-hydroxy-3-[N-isobutyl-(N-4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid [3R,3aS,6aR]-hexahydrofuro[2,3-b]furan-3-yl ester
622866-42-6

{(1S,2R)-[1-(4-formyl-benzyl)]-(2R)-2-hydroxy-3-[N-isobutyl-(N-4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid [3R,3aS,6aR]-hexahydrofuro[2,3-b]furan-3-yl ester

Conditions
ConditionsYield
Stage #1: C27H38N2O7S With methanesulfonic acid In tetrahydrofuran at 40℃;
Stage #2: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With 1-methyl-1H-imidazole In tetrahydrofuran at 50℃; Product distribution / selectivity;
70%
2-(2-Dimethylamino-ethylamino)-benzooxazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide
470704-95-1

2-(2-Dimethylamino-ethylamino)-benzooxazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

((1S,2R)-1-Benzyl-3-{[2-(2-dimethylamino-ethylamino)-benzooxazole-6-sulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

((1S,2R)-1-Benzyl-3-{[2-(2-dimethylamino-ethylamino)-benzooxazole-6-sulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;67%
C32H41N3O7S2
1007876-78-9

C32H41N3O7S2

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

C34H41N3O9S2

C34H41N3O9S2

Conditions
ConditionsYield
Stage #1: C32H41N3O7S2 With hydrogenchloride In 1,4-dioxane at 20℃; for 0.333333h;
Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane
Stage #3: 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione With N-ethyl-N,N-diisopropylamine
67%
2-(3-Dimethylamino-propylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

2-(3-Dimethylamino-propylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

((1S,2R)-1-Benzyl-3-{[2-(3-dimethylamino-propylamino)-benzothiazole-6-sulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

((1S,2R)-1-Benzyl-3-{[2-(3-dimethylamino-propylamino)-benzothiazole-6-sulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;66%
2-(2-Methylamino-ethylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

2-(2-Methylamino-ethylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

((1S,2R)-1-Benzyl-2-hydroxy-3-{isobutyl-[2-(2-methylamino-ethylamino)-benzothiazole-6-sulfonyl]-amino}-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

((1S,2R)-1-Benzyl-2-hydroxy-3-{isobutyl-[2-(2-methylamino-ethylamino)-benzothiazole-6-sulfonyl]-amino}-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;64%
N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-N-isobutyl-4-aminobenzenesulfonamide

N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-N-isobutyl-4-aminobenzenesulfonamide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-4-((4-amino-N-isobutylphenyl)-sulfonamido)-3-hydroxybutan-2-yl)carbamate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-4-((4-amino-N-isobutylphenyl)-sulfonamido)-3-hydroxybutan-2-yl)carbamate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 40h;62%
N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)[1-(2-methylpropyl)benzimidazol-6-yl]sulfonamide hydrochloride

N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)[1-(2-methylpropyl)benzimidazol-6-yl]sulfonamide hydrochloride

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

[(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[[1-(2-methylpropyl)benzimidazol-6-yl]sulfonyl]amino]-1-(phenylmethyl)propyl]carbamic acid [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

[(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[[1-(2-methylpropyl)benzimidazol-6-yl]sulfonyl]amino]-1-(phenylmethyl)propyl]carbamic acid [(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl] ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 4h;60%
2-(2-Dimethylamino-ethylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide
473739-12-7

2-(2-Dimethylamino-ethylamino)-benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

((1S,2R)-1-Benzyl-3-{[2-(2-dimethylamino-ethylamino)-benzothiazole-6-sulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

((1S,2R)-1-Benzyl-3-{[2-(2-dimethylamino-ethylamino)-benzothiazole-6-sulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;59%
C24H33N3O2S
1217206-75-1

C24H33N3O2S

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

C31H41N3O6S
1217206-85-3

C31H41N3O6S

Conditions
ConditionsYield
With triethylamine In dichloromethane59%
N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-N-isobutyl-4-methoxybenzenesulfonamide

N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-N-isobutyl-4-methoxybenzenesulfonamide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-3-hydroxy-4-((N-isobutyl-4-methoxyphenyl)sulfonamido)-butan-2-yl)carbamate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-3-hydroxy-4-((N-isobutyl-4-methoxyphenyl)sulfonamido)-butan-2-yl)carbamate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 48h;59%
N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-4-methoxy-N-phenylbenzenesulfonamide

N-((2R,3S)-4-(adamantan-1-yl)-3-amino-2-hydroxybutyl)-4-methoxy-N-phenylbenzenesulfonamide

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione
253265-97-3

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-3-hydroxy-4-((4-methoxy-N-phenylphenyl)sulfonamido)butan-2-yl)carbamate

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(adamantan-1-yl)-3-hydroxy-4-((4-methoxy-N-phenylphenyl)sulfonamido)butan-2-yl)carbamate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 58h;58%

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