(1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol

Base Information

• Chemical Name: (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol
• CAS No.: 201603-61-4
• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.419

Synonyms:(1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol

Chemical Property of (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol

There total 22 articles about (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol 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: 56.0%

(1S)-(1,3/2,4)-1,2-dibenzyloxy-3-hydroxy-4-hydroxymethylcyclohex-5-ene (118968-02-8) → (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol (201603-61-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 60h; Heating;

DOI:10.1021/jo051645q

Reference yield: 55.0%

(1S)-(1,3/2,4)-1,2-dibenzyloxy-3-hydroxy-4-hydroxymethylcyclohex-5-ene (118968-02-8) → (1S,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol + (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol (201603-61-4)

Guidance literature:

With sodium dihydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; at 50 ℃; for 18h; Inert atmosphere;

DOI:10.1002/ejoc.201402588

Reference yield: 10.0%

(1R,2R,3S,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-iodomethyl-7-oxa-bicyclo[4.1.0]heptane (201603-59-0) → ((1R,2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-7-oxabicyclo-[4.1.0]heptan-2-yl)methanol (+)-2,3,4-tri-O-benzylcyclophellitol (157761-58-5) + (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol (201603-61-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); oxygen; tri-n-butyl-tin hydride; In toluene; at 60 ℃; for 3h;

DOI:10.1021/jo971998s

upstream raw materials:

(1R,2R,3S,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-iodomethyl-7-oxa-bicyclo[4.1.0]heptane

(1S)-(1,3/2,4)-1,2-dibenzyloxy-3-hydroxy-4-hydroxymethylcyclohex-5-ene

2,3-di-O-benzyl-2,3-dihydroxypent-4-enal

methyl 2,3-di-O-benzyl-5-deoxy-5-iodo-D-xylofuranoside

Downstream raw materials:

cyclophellitol

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