((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

Base Information

• Chemical Name: ((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
• CAS No.: 157761-58-5
• Molecular Formula: C₂₈H₃₀O₅
• Molecular Weight: 446.543

Synonyms:((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

Chemical Property of ((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

Chemical Property:

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Technology Process of ((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

There total 66 articles about ((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 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: 94.0%

Methanesulfonic acid (1S,2R,3S,4R,5S,6R)-2,3,4-tris-benzyloxy-6-hydroxy-5-hydroxymethyl-cyclohexyl ester → ((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)

Guidance literature:

With sodium methylate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol035424n

Reference yield: 80.0%

(1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol (176380-10-2) → ((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)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1016/j.tetasy.2010.10.010

Reference yield: 78.0%

(1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol (176380-10-2) → ((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) + ((1S,2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-methanol

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(98)02274-6

upstream raw materials:

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

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

((1R,2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid

(1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol

Downstream raw materials:

(1S,2R,3S,4R,5R,6R)-2,3,4-tris(benzyloxy)-5-benzyloxymethyl-7-oxabicyclo<4.1.0>heptane

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