(3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate
• CAS No.: 1001547-69-8
• Molecular Formula: C₁₃H₁₅BrO₅S
• Molecular Weight: 363.229
• Mol file: 1001547-69-8.mol

Synonyms:(3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

Chemical Property of (3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

There total 4 articles about (3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 43.0%

(3R,3aS,6R,6aR)-6-hydroxy-3-(4-methoxyphenyl)sulfonyloxyperhydrofuro[3,2-b]furan (72631-59-5) → (3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (1001547-69-8)

Guidance literature:

With pyridine; carbon tetrabromide; triphenylphosphine; at 65 ℃; for 2h; Product distribution / selectivity;

Reference yield: 29.0%

(3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate) (54522-28-0,66966-12-9,67890-26-0,76793-35-6,107740-09-0) → (3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (1001547-69-8)

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; at 100 ℃; for 27h; Product distribution / selectivity;

Reference yield:

(3R,6R)-hexahydrofuro[3,2-b]furan-3,6-diol → (3R,3aS,6S,6aS)-6-bromohexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (1001547-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 2 h / 0 - 20 °C

2: pyridine; carbon tetrabromide; triphenylphosphine / N,N-dimethyl-formamide / 65 °C / Inert atmosphere

With pyridine; carbon tetrabromide; triphenylphosphine; In N,N-dimethyl-formamide;

upstream raw materials:

(3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate)

(3R,3aS,6R,6aR)-6-hydroxy-3-(4-methoxyphenyl)sulfonyloxyperhydrofuro[3,2-b]furan

p-toluenesulfonyl chloride

Downstream raw materials:

(3R,3aR,6S,6aS)-3-hydroxyhexahydro-2H-furo[3,2-b]pyrrol-6-yl 4-methylbenzenesulfonate

C₂₁H₂₃NO₇S

benzyl (S)-2-((S)-2,5-dihydrofuran-2-yl)-2-hydroxyethylcarbamate

(S)-2-(benzyloxycarbonylamino)-1-((S)-2,5-dihydrofuran-2-yl)ethyl 4-methylbenzenesulfonate