We product this chemical more than 10 years . We are very experience to export it to many countries, Our superior & stable quality , competitive price gain warm reception from our customers. Specification : (3R,3aS,6aR)-hexahydrofuro[2,3-b]
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inquiryDayangchem'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
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inquirySpecifications CAS No.: 156928-09-5 Other Names: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol MF: C6H10O3 EINECS No.: - Place of Origin:
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inquiryAccording to customer request Appearance:Pale Yellow Oil Storage:2-8°C Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:shanghai
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inquiry(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol CAS:156928-09-5 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in h
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inquiryHello, 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
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inquiryOur 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
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inquiryA 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
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Cas:156928-09-5
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inquiryIn stock (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol 156928-09-5Appearance:off-white powder Storage:room temperature Package:according to customers' requirements Application:Organic intermediates Transportation:By air(EMS or EUB or FedEx or TNT ect..
Cas:156928-09-5
Min.Order:1 Gram
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inquiryWe 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
Cas:156928-09-5
Min.Order:100 Gram
FOB Price: $100.0 / 2000.0
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inquirySuperior quality, moderate price & quick delivery. Appearance:white powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:10g/bag,or as your request Application:Used as Pharmaceutical Intermediates Transporta
Cas:156928-09-5
Min.Order:1 Gram
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Type:Trading Company
inquiryProduct name: (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol CAS No.:156928-09-5 Molecule Formula:C6H10O3 Molecule Weight:130.14 Purity: 96.0% Package: 200kg/drum Description:Colorless to light yellow liquid Manufacture Standards:Enterpr
Cas:156928-09-5
Min.Order:1 Kilogram
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Type:Trading Company
inquiryOur Advantages A. International Top level TechnologyOur company owned biomedicine experts are famous at home and abroad with rich experience in research and development in the field of efficient chiral functional molecules research and development an
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inquiryHANGZHOU 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
Cas:156928-09-5
Min.Order:1 Gram
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inquiryfactory?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
Cas:156928-09-5
Min.Order:1 Kilogram
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Type:Trading Company
inquiry3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With methanol; potassium carbonate at 20℃; Product distribution / selectivity; | 100% |
With potassium carbonate In methanol at 20℃; | 30% |
With methyllithium In tetrahydrofuran |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
Stage #1: (2R,3S)-3-dimethoxymethyl-5-benzyloxy-1,2-pentanediol With sulfuric acid In toluene at 0 - 35℃; for 15.5h; Stage #2: With palladium 10% on activated carbon; hydrogen at 25℃; for 6h; Stage #3: at 72 - 197℃; for 4.5h; | 99% |
(3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one
A
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
B
(3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan
Conditions | Yield |
---|---|
Stage #1: (3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one With sodium tetrahydroborate In methanol; isopropyl alcohol at 0℃; for 1.5h; Stage #2: With ammonium chloride In methanol; isopropyl alcohol Product distribution / selectivity; | A 97.2% B n/a |
Stage #1: (3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one With sodium tetrahydroborate In ethanol at -15℃; for 2h; Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity; |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With methanol; water; sodium hydroxide In tetrahydrofuran at 20℃; for 0.5h; | 95% |
With sodium hydroxide In water at 27 - 30℃; for 4h; | 93% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With hydrogenchloride; diisobutylaluminium hydride In water; toluene at -50 - 60℃; for 16h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; | 95% |
With diisobutylaluminium hydride In toluene at -50 - 40℃; Inert atmosphere; | 56.4 g |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol under 760.051 Torr; for 1h; Solvent; | 91% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With hydrogenchloride In water at -2 - 5℃; Temperature; | 90.4% |
A
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
B
3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran
C
Acetic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester
Conditions | Yield |
---|---|
With acetic anhydride In tert-butyl methyl ether at 20℃; for 110h; Reagent/catalyst; Enzymatic reaction; | A 90% B n/a C n/a |
With acetic anhydride In 1,2-dimethoxyethane at 23℃; for 3h; Yield given. Yields of byproduct given; |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 24h; Reagent/catalyst; | 90% |
With lipase Enzymatic reaction; |
A
(3S,3aR,6aS)-3-hydroxyhexahydrofuro<2,3-b>furan
B
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
C
3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran
D
Acetic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester
Conditions | Yield |
---|---|
With acetic anhydride In tert-butyl methyl ether at 20℃; for 110h; Reagent/catalyst; Enzymatic reaction; | A n/a B 90% C n/a D n/a |
A
(3S,3aR,6aS)-3-hydroxyhexahydrofuro<2,3-b>furan
B
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With acetic anhydride In tert-butyl methyl ether at 20℃; for 110h; Reagent/catalyst; Enzymatic reaction; | A 90% B n/a |
vinyl acetate
A
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With Chirazyme L-2 In tert-butyl methyl ether at 25℃; for 40h; Enzymatic reaction; | A 90% B n/a |
((R)-1-Naphthalen-1-yl-ethyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; | 86% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With sodium methylate In methanol Mitsunobu Displacement; Inert atmosphere; stereoselective reaction; | 82% |
With lithium hydroxide; triethylamine In methanol; water at 23℃; for 2h; | 326 mg |
(3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
Stage #1: (3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan With di-isopropyl azodicarboxylate; triphenylphosphine; 4-nitro-benzoic acid In benzene at 23℃; for 1.5h; Mitsunobu reaction; Stage #2: With lithium hydroxide; triethylamine In methanol; water at 20℃; for 2h; | 82% |
Multi-step reaction with 2 steps 1: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 2: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C View Scheme | |
Multi-step reaction with 2 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 View Scheme |
(3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at -15 - 20℃; for 3h; | 81% |
With sodium tetrahydroborate; ethanol at 0℃; for 0.5h; | 80% |
With sodium tetrahydroborate In ethanol at -18℃; for 2.5h; | 70% |
With sodium tetrahydroborate In ethanol at -18℃; for 2.5h; | 70% |
(2R,3R)-1,2-O-isopropylidene-3-vinyl-1,2,5-pentanetriol
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
Stage #1: (2R,3R)-1,2-O-isopropylidene-3-vinyl-1,2,5-pentanetriol With ozone Stage #2: With toluene-4-sulfonic acid | 80% |
Stage #1: (2R,3R)-1,2-O-isopropylidene-3-vinyl-1,2,5-pentanetriol With dimethylsulfide; ozone In methanol; dichloromethane at -78 - 20℃; for 3h; Inert atmosphere; Stage #2: toluene-4-sulfonic acid In methanol; chloroform for 1h; Reflux; | 80% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran at 50℃; for 6h; Solvent; | 77% |
(3aS,4S,6aR)-4-methoxy-tetrahydro-furo[3.4-b]furan-2(3H)-one
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
Stage #1: (3aS,4S,6aR)-4-methoxy-tetrahydro-furo[3.4-b]furan-2(3H)-one With lithium borohydride In tetrahydrofuran at 50℃; for 2.5h; Stage #2: With hydrogenchloride In tetrahydrofuran at -10℃; for 2h; | 76% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
Stage #1: ethyl (2R,3S)-3-(methyl(phenyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran Stage #2: With sulfuric acid In dichloromethane; water; ethyl acetate; toluene at -10 - 80℃; for 68.15h; | 75% |
Stage #1: ethyl (2R,3S)-3-(methyl(phenyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 20℃; for 17.25h; Stage #2: With sulfuric acid In tetrahydrofuran at -8 - 5℃; for 2h; | n/a |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at -15 - -5℃; | 73.77% |
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / 22 - 26 °C 2: sodium carbonate; methanol / 22 - 26 °C 3: hydrogenchloride / water / -2 - 5 °C View Scheme |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; water at 60℃; for 6h; Solvent; Temperature; | 72% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
Stage #1: (3aS,6aR)-4-methoxytetrahydrofuro[3,4-b]furan-2(3H)-one With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 23℃; for 1h; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 0℃; for 1.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 23℃; for 1h; | 63% |
Stage #1: (3aS,6aR)-4-methoxytetrahydrofuro[3,4-b]furan-2(3H)-one With sodium tetrahydroborate; lithium chloride In tetrahydrofuran at 25℃; Inert atmosphere; Reflux; Large scale; Stage #2: With hydrogenchloride In water at 10℃; for 2h; pH=1 - 3; Reagent/catalyst; Solvent; Inert atmosphere; Large scale; | 80 kg |
(3S,4'R)-3-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)tetrahydrofuran-2-ol
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
Stage #1: (3S,4'R)-3-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)tetrahydrofuran-2-ol With hydrogenchloride In tetrahydrofuran; water at 20℃; for 23h; Stage #2: With potassium carbonate In tetrahydrofuran; water for 0.333333h; | 61% |
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 16h; | |
With hydrogenchloride; sodium bicarbonate; sodium chloride In tetrahydrofuran; water |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
Stage #1: ethyl (2R,3S)-3-(ethyl(phenyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16h; Stage #2: With sulfuric acid In tetrahydrofuran at 20℃; for 3h; | 54% |
vinyl acetate
A
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
B
Acetic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester
Conditions | Yield |
---|---|
With Lipase PS at 50℃; for 24h; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | A 37% B 53% |
vinyl acetate
A
(3S,3aR,6aS)-3-hydroxyhexahydrofuro<2,3-b>furan
B
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
C
Acetic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester
Conditions | Yield |
---|---|
With lipase AS at 50℃; for 24h; Enzymatic reaction; enantioselective reaction; | A n/a B 30% C 51% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In tetrahydrofuran at -74℃; for 1h; Temperature; Solvent; Inert atmosphere; | 50% |
ethyl (2R,3S)-3-(methoxy(methyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
Stage #1: ethyl (2R,3S)-3-(methoxy(methyl)carbamoyl)-5-oxotetrahydrofuran-2-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16h; Stage #2: With sulfuric acid In tetrahydrofuran at 20℃; for 3h; | 50% |
acetic anhydride
A
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
B
Acetic acid (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at 23℃; immobilized Amano lipase; | A n/a B 45% |
Amano lipase 30 immobilized on Celite 521 In 1,2-dimethoxyethane at 23℃; Resolution of racemate; | A 42% B 45% |
Amano lipase PS-C I In 1,2-dimethoxyethane Purification / work up; Resolution of racemate; | A 32% B n/a |
With porcine pancreatic lipase (PPL) In tert-butyl methyl ether at 20℃; for 110h; Reagent/catalyst; Enzymatic reaction; |
benzoyl chloride
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 7h; enantioselective reaction; | 97% |
4-Nitrophenyl chloroformate
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 23℃; for 12h; Inert atmosphere; | 92% |
With pyridine In dichloromethane | 89% |
With pyridine In ethyl acetate at 0℃; for 1h; | 51.8% |
4-aminobenzenesulfonyl chloride
isobutylamine
1,1'-carbonyldiimidazole
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
Stage #1: 1,1'-carbonyldiimidazole; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol In tetrahydrofuran for 1h; Stage #2: (S)-3-amino-(S)-2-hydroxy-4-phenyl-1-chlorobutane hydrochloride In tetrahydrofuran at 55 - 60℃; Stage #3: 4-aminobenzenesulfonyl chloride; isobutylamine | 92% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
4-nitro-benzoic acid
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate
Conditions | Yield |
---|---|
With pyridine; triethylamine at 0 - 20℃; | 92% |
di(succinimido) carbonate
(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
Conditions | Yield |
---|---|
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% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
C6H9IO2
Conditions | Yield |
---|---|
With iodine; triphenylphosphine | 90% |
Conditions | Yield |
---|---|
With pyridine; triethylamine at 0 - 20℃; Reagent/catalyst; | 90% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
(3S,3aR,6aR)-3-Iodo-hexahydro-furo[2,3-b]furan
Conditions | Yield |
---|---|
With 1H-imidazole; iodine; triphenylphosphine In benzene at 60℃; | 87% |
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
(3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; Dess-Martin periodane In dichloromethane at 0 - 23℃; Dess-Martin oxidation; Inert atmosphere; | 87% |
With disodium hydrogenphosphate; Dess-Martin periodane In dichloromethane at 0 - 23℃; for 3h; Inert atmosphere; | 87% |
With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In dichloromethane at 23℃; for 1h; Molecular sieve; | |
With disodium hydrogenphosphate; Dess-Martin periodane In dichloromethane at 0 - 23℃; Inert atmosphere; |
4-Nitrophenyl chloroformate
(3S,3aR,6aS)-3-hydroxyhexahydrofuro<2,3-b>furan
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
(3R,3aS,6aR) and (3S,3aR,6aS)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate
Conditions | Yield |
---|---|
With 4-methyl-morpholine In dichloromethane at 0℃; for 16h; | 86% |
N-hydroxyphthalimide
bis(trichloromethyl) carbonate
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol With pyridine In dichloromethane at 55℃; for 3h; Stage #2: N-hydroxyphthalimide In dichloromethane at 50℃; for 4h; Stage #3: N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride In toluene at 50℃; for 6h; | 85.8% |
trifluoromethylsulfonic anhydride
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0 - 20℃; | 85% |
1-hydroxy-pyrrolidine-2,5-dione
bis(trichloromethyl) carbonate
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol With triethylamine In toluene at 90℃; for 3h; Stage #2: 1-hydroxy-pyrrolidine-2,5-dione In ethyl acetate at 50℃; for 3h; Stage #3: N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride In toluene at 50℃; for 6h; | 84.9% |
di(succinimido) carbonate
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide
Conditions | Yield |
---|---|
With pyridine; triethylamine; methylamine In ethanol; water; acetonitrile Product distribution / selectivity; | 81% |
With triethylamine; methylamine In ethanol; water; ethyl acetate; acetonitrile | 71% |
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℃; |
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