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Hangzhou Maytime Bio-Tech Co.,Ltd.

we are supplying below two darunavir intermediates. 4-Amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide CAS:169280-56-2 (3aS,4S,6aR)-Tetrahydro-4-methoxy-furo[3,4-b]furan-2(3H)-one CAS:866594-60-7 Appearance

Darunavir intermediate CAS:169280-56-2

Cas:169280-56-2

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

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

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

Cas:169280-56-2

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

Kono Chem Co.,Ltd

Specifications CAS No.: 169280-56-2 Other Names: Ethyl propiolate MF: C20H29N3O3S EINECS No.: 169280-56-2 Place of Origin: Shandong,

CAS NO. 169280-56-2 4-amino-n-[(2r,3s)-3-amino-2-hydroxy-4-phenylbutyl]-n-isobutylbenzene-1-sulfonamide,

Cas:169280-56-2

Min.Order:1 Kilogram

FOB Price: $300.0 / 400.0

Type:Other

inquiry

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

Darunavir intermediate manufacturer/supplier

Cas:169280-56-2

Min.Order:1 Gram

Negotiable

Type:Manufacturers

inquiry

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

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

Cas:169280-56-2

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufactu

4-AMINO-N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-N-ISOBUTYLBENZENE-1-SULFONAMIDE CAS 169280-56-2

Cas:169280-56-2

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

Type:Trading Company

inquiry

Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O

C20H29N3O3S 4-AMINO-N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-N-ISOBUTYLBENZENE-1-SULFONAMIDE 169280-56-2

Cas:169280-56-2

Min.Order:1 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

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 169280-56-2 with competitive price

Cas:169280-56-2

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

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

4-AMINO-N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-N-ISOBUTYLBENZENE-1-SULFONAMIDE CAS NO.169280-56-2

Cas:169280-56-2

Min.Order:1 Kilogram

FOB Price: $5.0

Type:Lab/Research institutions

inquiry

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

Benzenesulfonamide,4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)- 169280-56-2

Cas:169280-56-2

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Qingdao Beluga Import and Export Co., LTD

4-AMINO-N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-N-ISOBUTYLBENZENE-1-SULFONAMIDE CAS:169280-56-2 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of c

4-AMINO-N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-N-ISOBUTYLBENZENE-1-SULFONAMIDE CAS:169280-56-2

Cas:169280-56-2

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

Benzenesulfonamide,4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-

Cas:169280-56-2

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Hisunny Chemical Co.,Ltd

Best quality & Attractive price & Professional service; Trial & Pilot & Commercial Hisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, specia

4-Amino-N-((2R,3S)-3-Amino-2-Hydroxy-4-Phenylbutyl)-N-Isobutylbenzenesulfonamide

Cas:169280-56-2

Min.Order:0

Negotiable

Type:Manufacturers

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

4-Amino-N-[(2r,3s)-3-Amino-2-Hydroxy-4-Phenyl butyl]-N-Isobutylbenzenesulfonamide(D7)

Cas:169280-56-2

Min.Order:100 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter

4-Amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide

Cas:169280-56-2

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

Darunavir intermediate 2

Cas:169280-56-2

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

HANWAYS CHEMPHARM CO.,LIMITED

We are concentrating on the R&D and technical service of APIs and pharmaceutical intermediates Application:Pharmaceutical intermediate Port:Chinese main port

China supplier high quality Darunavir intermediate 2 in stock

Cas:169280-56-2

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide

Cas:169280-56-2

Min.Order:4 Kilogram

Negotiable

Type:Lab/Research institutions

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

Benzenesulfonamide,4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-

Cas:169280-56-2

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Massive Chemical Technology Co., Ltd.

Massive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and

4-AMINO-N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-N-ISOBUTYLBENZENE-1-SULFONAMIDE/High quality/Best price

Cas:169280-56-2

Min.Order:1 Gram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

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

Darunavir intermediate

Cas:169280-56-2

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Siwei Development Group Ltd.

Product name: 4-Amino-N-(2R,3S)-3-Amino-2-Hydroxy-4-Phenyl-Butyl)-N-Isobutylbenzenesulfonamide CAS No.:169280-56-2 Molecule Formula:C20H29N3O3S Molecule Weight:391.52 Purity: 99% Package: 25kg/drum Description:White crystalline powder Manufact

High Quality 4-Amino-N-(2R,3S)-3-Amino-2-Hydroxy-4-Phenyl-Butyl)-N-Isobutylbenzenesulfonamide in stock

Cas:169280-56-2

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

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

Cas:169280-56-2

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

Hangzhou Think Chemical Co. Ltd

HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufacture. With about ten years of business experiences on the marketing & distribution, thinkchem specializes in exp

EAST CHEMSOURCES LIMITED

factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B

Darunavir intermediate 2

Cas:169280-56-2

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology 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 chemicals. W

Darunavir intermediate 2

Cas:169280-56-2

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

Darunavir intermediate 2

Cas:169280-56-2

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

inquiry

Hangzhou Zhongqi chem Co.,Ltd.

Located in Hangzhou National Hi-Tech Industrial Development Zone, zhongqichem is a technical company mainly focus on the Custom synthesis, manufacturing, sales of chemicals to various industries. Benefiting from the outstanding customer service and h

Synthetic route

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
191226-98-9

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

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

Conditions
ConditionsYield
Stage #1: [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester With palladium 10% on activated carbon; ammonium formate; acetic acid In tetrahydrofuran at 15 - 20℃; Large scale;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 35 - 45℃; Large scale;
99.4%
Stage #1: [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester With triethanolamine; hydrogen; palladium 10% on activated carbon In methanol at 40 - 45℃; for 2h;
Stage #2: With hydrogenchloride; water for 2h; Reflux;
Stage #3: With sodium hydroxide In water; isopropyl alcohol at 20℃; for 10h; pH=9 - 10;
95%
Multi-step reaction with 2 steps
1: 95 percent / H2 / Pd/C / ethyl acetate / 11 h / 23 °C
2: CF3COOH / CH2Cl2 / 0.67 h / 23 °C
View Scheme
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

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

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 4h;96%
With trifluoroacetic acid In dichloromethane at 23℃; for 0.666667h;
With trifluoroacetic acid In dichloromethane at 20℃;0.75 g
N-(3-dibenzylamino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitrobenzenesulfonamide
244641-42-7

N-(3-dibenzylamino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitrobenzenesulfonamide

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

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃;95%
With hydrogen; palladium dihydroxide In methanol at 23℃; for 4h; Catalytic hydrogenation; hydrogenolysis;
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

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

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2585.81 Torr; for 2h; Inert atmosphere;94%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2585.81 Torr; for 2h;94%
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; under 2585.81 Torr; for 2h;94%
4-nitro-N-((2R(syn),3S)-3-(N-benzyloxycarbonylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide
159005-59-1

4-nitro-N-((2R(syn),3S)-3-(N-benzyloxycarbonylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide

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

Conditions
ConditionsYield
With hydrogen; palladium(II) hydroxide/carbon In methanol at 40℃; under 760.051 Torr; for 3.5h;91%
With hydrogen; palladium(II) hydroxide/carbon In methanol at 40℃; under 760.051 Torr; for 3 - 5.5h;90%
Stage #1: 4-nitro-N-((2R(syn),3S)-3-(N-benzyloxycarbonylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide With hydrogenchloride; hydrogen; palladium(II) hydroxide/carbon In methanol; water at 40℃; under 760.051 Torr; for 21h;
Stage #2: With sodium hydroxide In water at 4℃; for 5.7h;
71%
1-benzyl-2-hydroxy-3-([isobutyl-(4-aminobenzenesulfonyl)amino]propyl)carbamic acid tert-butyl ester oxalate

1-benzyl-2-hydroxy-3-([isobutyl-(4-aminobenzenesulfonyl)amino]propyl)carbamic acid tert-butyl ester oxalate

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

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 25 - 35℃; Solvent; Reagent/catalyst;89.6%
(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane
143224-62-8

(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

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

Conditions
ConditionsYield
Stage #1: (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane; 4-Nitrobenzenesulfonyl chloride With triethylamine In ethyl acetate at 40℃; for 3h;
Stage #2: With hydrogen; 5% Pd(OH)2/C In methanol at 40℃; under 760.051 Torr; for 5h;
87%
4-amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide sulphate salt

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

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

Conditions
ConditionsYield
With potassium carbonate In water at 50 - 60℃; for 3h;76.39%
(2R,3S)-N-isobutyl-N-(2-hydroxy-3-azido-4-phenylbutyl)-p-nitrobenzenesulfonylamide

(2R,3S)-N-isobutyl-N-(2-hydroxy-3-azido-4-phenylbutyl)-p-nitrobenzenesulfonylamide

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

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate
(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester
98760-08-8, 98818-34-9, 98818-35-0, 103127-56-6, 98737-29-2

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: propan-2-ol / 2 h / 80 °C
2: 0.88 g / triethylamine / CH2Cl2 / 4 h / 20 °C
3: H2 / Pd(OH)2 on carbon / ethyl acetate / 1 h
4: 0.75 g / trifluoroacetic acid / CH2Cl2 / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 97 percent / propan-2-ol / 3 h / 80 °C
2: 90 percent / Et3N / CH2Cl2 / 16 h
3: 95 percent / H2 / Pd(OH)2 / ethyl acetate / 4 h
4: 96 percent / TFA / CH2Cl2 / 4 h
View Scheme
Multi-step reaction with 4 steps
1: 99 percent / propan-2-ol / 6 h / Heating
2: 96 percent / NaHCO3 / H2O; CH2Cl2 / 12 h / 23 °C
3: 95 percent / H2 / Pd/C / ethyl acetate / 11 h / 23 °C
4: CF3CO2H / CH2Cl2 / 0.67 h / 23 °C
View Scheme
(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol
160232-08-6

(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0.88 g / triethylamine / CH2Cl2 / 4 h / 20 °C
2: H2 / Pd(OH)2 on carbon / ethyl acetate / 1 h
3: 0.75 g / trifluoroacetic acid / CH2Cl2 / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 90 percent / Et3N / CH2Cl2 / 16 h
2: 95 percent / H2 / Pd(OH)2 / ethyl acetate / 4 h
3: 96 percent / TFA / CH2Cl2 / 4 h
View Scheme
Multi-step reaction with 3 steps
1: 96 percent / NaHCO3 / H2O; CH2Cl2 / 12 h / 23 °C
2: 95 percent / H2 / Pd/C / ethyl acetate / 11 h / 23 °C
3: CF3CO2H / CH2Cl2 / 0.67 h / 23 °C
View Scheme
βS--αR-<<(2-methylpropyl)amino>methyl>-benzenepropanol
169331-42-4

βS--αR-<<(2-methylpropyl)amino>methyl>-benzenepropanol

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / Et3N / CH2Cl2 / 4 h / 20 °C
2: 95 percent / H2 / Pd/C / methanol / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / Et3N / CH2Cl2 / 2 h / 23 °C
2: H2 / Pd(OH)2/C / methanol / 4 h / 23 °C
View Scheme
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

sodium-salt of 3-methyl-crotonamide

sodium-salt of 3-methyl-crotonamide

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / Et3N / CH2Cl2 / 4 h / 20 °C
2: 95 percent / H2 / Pd/C / methanol / 20 °C
View Scheme
(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane
143224-62-8

(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / Et3N / CH2Cl2 / 0 - 20 °C
2: 70 percent / H2 / Pd/C / ethyl acetate
View Scheme
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / Et3N / CH2Cl2 / 0 - 20 °C
2: 70 percent / H2 / Pd/C / ethyl acetate
View Scheme
Multi-step reaction with 2 steps
1.1: 3 h / Heating
1.2: Reflux
2.1: hydrogen; triethanolamine / palladium 10% on activated carbon / methanol / 2 h / 40 - 45 °C
2.2: 2 h / Reflux
2.3: 10 h / 20 °C / pH 9 - 10
View Scheme
Multi-step reaction with 4 steps
1.1: 1,4-dioxane / 1 h / 10 - 25 °C
2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 6 h / 80 - 85 °C
3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 - 25 °C
3.2: pH 8.5 - 9.2
4.1: hydrogen; palladium 10% on activated carbon / ethanol / 0.58 h / 20 - 25 °C / 2068.65 Torr
View Scheme
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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 86 percent / KF; O(9)-benzyl-N-(9-anthracenylmethyl)cinchonidium fluoride / tetrahydrofuran / 6 h / -10 °C
2: 85 percent / NaBH4; NiCl2 / methanol / 0.17 h / 0 °C
3: MgSO4
4: NaBH4 / ethanol / 4 h / 0 - 23 °C
5: 94 percent / Et3N / CH2Cl2 / 2 h / 23 °C
6: H2 / Pd(OH)2/C / methanol / 4 h / 23 °C
View Scheme
(2R,3S)-3-(dibenzylamino)-1-nitro-4-phenylbutan-2-ol
244641-41-6

(2R,3S)-3-(dibenzylamino)-1-nitro-4-phenylbutan-2-ol

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 85 percent / NaBH4; NiCl2 / methanol / 0.17 h / 0 °C
2: MgSO4
3: NaBH4 / ethanol / 4 h / 0 - 23 °C
4: 94 percent / Et3N / CH2Cl2 / 2 h / 23 °C
5: H2 / Pd(OH)2/C / methanol / 4 h / 23 °C
View Scheme
(2R,3S)-1-amino-3-(dibenzylamino)-4-phenylbutan-2-ol
170359-24-7

(2R,3S)-1-amino-3-(dibenzylamino)-4-phenylbutan-2-ol

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: MgSO4
2: NaBH4 / ethanol / 4 h / 0 - 23 °C
3: 94 percent / Et3N / CH2Cl2 / 2 h / 23 °C
4: H2 / Pd(OH)2/C / methanol / 4 h / 23 °C
View Scheme
(2R,3S)-3-Dibenzylamino-1-[2-methyl-prop-(E)-ylideneamino]-4-phenyl-butan-2-ol

(2R,3S)-3-Dibenzylamino-1-[2-methyl-prop-(E)-ylideneamino]-4-phenyl-butan-2-ol

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaBH4 / ethanol / 4 h / 0 - 23 °C
2: 94 percent / Et3N / CH2Cl2 / 2 h / 23 °C
3: H2 / Pd(OH)2/C / methanol / 4 h / 23 °C
View Scheme
(2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane
136465-89-9

(2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: propan-2-ol / 12 h / 80 °C
2: aq. NaHCO3
3: H2 / 10percent Pd/C / ethyl acetate
View Scheme
(2R,3R)-3-azido-4-phenylbutane-1,2-diol
206361-96-8

(2R,3R)-3-azido-4-phenylbutane-1,2-diol

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaHCO3
2: H2 / 10percent Pd/C / ethyl acetate
View Scheme
[(1S,2R)-3-[(4-aminophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]amine hydrochloride
1415750-61-6

[(1S,2R)-3-[(4-aminophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]amine hydrochloride

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

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 0 - 7℃; for 4 - 48h; pH=> 12.5;
With sodium carbonate In dichloromethane; water at 20 - 25℃; for 0.333333h;11.2 g
tert-butyl ((2S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
1229623-13-5

tert-butyl ((2S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydrogencarbonate / dichloromethane / 5 h / Reflux
2.1: triethylamine / dichloromethane / Reflux
2.2: Reflux
3.1: hydrogen; triethanolamine / palladium 10% on activated carbon / methanol / 2 h / 40 - 45 °C
3.2: 2 h / Reflux
3.3: 10 h / 20 °C / pH 9 - 10
View Scheme
N-(tert-butoxycarbonyl)-L-phenylalanine chlorohydrine

N-(tert-butoxycarbonyl)-L-phenylalanine chlorohydrine

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydrogencarbonate / dichloromethane / 5 h / Reflux
2: triethylamine / dichloromethane / Reflux
3: hydrogen; triethanolamine / palladium 10% on activated carbon / methanol / 2 h / 40 - 45 °C
4: hydrogenchloride; water / 2 h / Reflux
View Scheme
N-isobutyl-4-nitrobenzenesulfonamide
89840-80-2

N-isobutyl-4-nitrobenzenesulfonamide

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 6 h / 80 - 85 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 - 25 °C
2.2: pH 8.5 - 9.2
3.1: hydrogen; palladium 10% on activated carbon / ethanol / 0.58 h / 20 - 25 °C / 2068.65 Torr
View Scheme
4-aminobenzenesulfonyl chloride
24939-24-0

4-aminobenzenesulfonyl chloride

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1,4-dioxane / 0.83 h / 5 - 25 °C
2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 6 h / 80 - 85 °C
3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 - 25 °C
3.2: pH 8.5 - 9
View Scheme
4-amino-N-isobutylbenzenesulfonamide
53668-36-3

4-amino-N-isobutylbenzenesulfonamide

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 6 h / 80 - 85 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 - 25 °C
2.2: pH 8.5 - 9
View Scheme
N-(4-Isobutylsulfamoyl-phenyl)-acetamide
72225-62-8

N-(4-Isobutylsulfamoyl-phenyl)-acetamide

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 14 h / 85 - 90 °C
2.1: hydrogenchloride; water / ethanol / 10 h / 55 - 65 °C
2.2: 0.5 h / 25 - 30 °C / pH 11.5 - 12.5
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 14 h / 85 - 90 °C
2.1: trifluoroacetic acid / dichloromethane / 5 h / 20 - 25 °C
2.2: pH 9.11
3.1: hydrogenchloride / water; ethanol / 6.5 h / 60 - 65 °C
4.1: sodium carbonate / dichloromethane; water / 0.33 h / 20 - 25 °C
View Scheme
p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1,4-dioxane / 3.58 h / 5 - 25 °C
2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 14 h / 85 - 90 °C
3.1: hydrogenchloride; water / ethanol / 10 h / 55 - 65 °C
3.2: 0.5 h / 25 - 30 °C / pH 11.5 - 12.5
View Scheme
Multi-step reaction with 5 steps
1.1: 1,4-dioxane / 3.58 h / 5 - 25 °C
2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 14 h / 85 - 90 °C
3.1: trifluoroacetic acid / dichloromethane / 5 h / 20 - 25 °C
3.2: pH 9.11
4.1: hydrogenchloride / water; ethanol / 6.5 h / 60 - 65 °C
5.1: sodium carbonate / dichloromethane; water / 0.33 h / 20 - 25 °C
View Scheme
tert-butyl (R)-3-((((4-nitrophenoxy)carbonyl)oxy)methyl)piperidine-1-carboxylate

tert-butyl (R)-3-((((4-nitrophenoxy)carbonyl)oxy)methyl)piperidine-1-carboxylate

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

tert-butyl (R)-3-(((((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)oxy)methyl)piperidine-1-carboxylate

tert-butyl (R)-3-(((((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)oxy)methyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 25℃; for 5h; Inert atmosphere;98.2%
C12H15NO7

C12H15NO7

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

(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl carbamate
1262482-52-9

(3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-yl-(2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; for 1h; Inert atmosphere;96%
N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid
84358-13-4

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

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

tert-butyl 4-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

tert-butyl 4-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 8h; Inert atmosphere;95.4%
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%
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

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

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

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 16h;94%
With triethylamine In tetrahydrofuran for 16h;94%
(3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid
88495-54-9

(3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid

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

tert-butyl (S)-3-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

tert-butyl (S)-3-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 8h; Inert atmosphere;93.4%
C19H20N2O9

C19H20N2O9

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

C35H44N4O9S

C35H44N4O9S

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 25h;90%
7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid
779-27-1

7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid

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

C30H33N3O7S

C30H33N3O7S

Conditions
ConditionsYield
Stage #1: 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
88%
C14H15NO8
1609973-50-3

C14H15NO8

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

C28H39N3O8S
1609973-55-8

C28H39N3O8S

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 30h;85%
tert-butyl (S)-3-((((4-nitrophenoxy)carbonyl)oxy)methyl)piperidine-1-carboxylate

tert-butyl (S)-3-((((4-nitrophenoxy)carbonyl)oxy)methyl)piperidine-1-carboxylate

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

tert-butyl (S)-3-(((((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)oxy)methyl)piperidine-1-carboxylate

tert-butyl (S)-3-(((((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)oxy)methyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 25℃; for 5h; Inert atmosphere;84.9%
2-oxo-2H-benzopyran-6-carboxylic acid
7734-80-7

2-oxo-2H-benzopyran-6-carboxylic acid

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

C30H33N3O6S

C30H33N3O6S

Conditions
ConditionsYield
Stage #1: 2-oxo-2H-benzopyran-6-carboxylic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
84%
7-methoxycoumarin-3-carboxylic acid
20300-59-8

7-methoxycoumarin-3-carboxylic acid

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

C31H35N3O7S

C31H35N3O7S

Conditions
ConditionsYield
Stage #1: 7-methoxycoumarin-3-carboxylic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
83%
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid
192725-55-6

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

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 1-methyl-pyrrolidin-2-one at -4 - 30℃; for 10h;82.5%
ethanol
64-17-5

ethanol

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid
192725-55-6

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

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

[14C]-Darunavir ethanolate
635728-49-3

[14C]-Darunavir ethanolate

Conditions
ConditionsYield
Stage #1: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide In 1-methyl-pyrrolidin-2-one at -4 - 30℃; for 10h;
Stage #2: ethanol at 45 - 50℃; for 1h;
82.5%
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

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
With pyridine; triethylamine; methylamine In ethanol; water; acetonitrile Product distribution / selectivity;81%
With triethylamine; methylamine In ethanol; water; ethyl acetate; acetonitrile71%
Stage #1: di(succinimido) carbonate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol With pyridine In acetonitrile at 25 - 30℃; for 1h;
Stage #2: 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide In acetonitrile at 0 - 5℃; for 0.5h;
Stage #3: With triethylamine; methylamine In acetonitrile at 0 - 30℃;
bis-(p-nitrophenyl) carbonate
5070-13-3

bis-(p-nitrophenyl) carbonate

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

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

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
With triethylamine; methylamine In ethanol; water; ethyl acetate; acetonitrile Product distribution / selectivity;81%
dihydrosinapic acid
14897-78-0

dihydrosinapic acid

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

N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-3-(4-hydroxy-3,5-dimethoxyphenyl)propanamide

N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-3-(4-hydroxy-3,5-dimethoxyphenyl)propanamide

Conditions
ConditionsYield
Stage #1: dihydrosinapic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere;
81%
(3S,7aS,8S)-hexahydro-4H-3,5-methanofuro[2,3-b]pyran-8-yl (4-nitrophenyl)carbonate

(3S,7aS,8S)-hexahydro-4H-3,5-methanofuro[2,3-b]pyran-8-yl (4-nitrophenyl)carbonate

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

(3S,7aS,8S)-hexahydro-4H-3,5-methanofuro[2,3-b]pyran-8-yl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate

(3S,7aS,8S)-hexahydro-4H-3,5-methanofuro[2,3-b]pyran-8-yl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 23℃; for 144h;80%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 23℃; for 72h; Inert atmosphere;80%
2-amino-6-chloro-9-carboxymethylpurine
149376-70-5

2-amino-6-chloro-9-carboxymethylpurine

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

2-(2-amino-6-chloro-9H-purin-9-yl)-N-((2S,3R)-4-(4-amino-N- isobutylphenylsulfonamido)-3- hydroxy-1-phenylbutan-2-yl)acetamide

2-(2-amino-6-chloro-9H-purin-9-yl)-N-((2S,3R)-4-(4-amino-N- isobutylphenylsulfonamido)-3- hydroxy-1-phenylbutan-2-yl)acetamide

Conditions
ConditionsYield
Stage #1: 2-amino-6-chloro-9-carboxymethylpurine; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
80%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

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

(E)-N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

(E)-N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 1.16667h; Inert atmosphere;
Stage #2: With dmap In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere;
80%
(R)-1-Boc-nipecotic acid
163438-09-3

(R)-1-Boc-nipecotic acid

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

tert-butyl (R)-3-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

tert-butyl (R)-3-(((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamoyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 8h; Inert atmosphere;79.4%
C13H12N2O10
1609973-49-0

C13H12N2O10

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

C27H36N4O10S
1609973-54-7

C27H36N4O10S

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 30h;79%
2-((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)acetic acid

2-((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)acetic acid

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

N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-2-((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)acetamide
1075209-51-6

N-((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-2-((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)acetamide

Conditions
ConditionsYield
Stage #1: 2-((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl)acetic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 0.0833333h;
Stage #2: With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 23℃; for 24h;
79%

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