(1R,2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

Base Information

• Chemical Name: (1R,2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol
• CAS No.: 120595-81-5
• Molecular Formula: C₃₂H₄₆O₆Si
• Molecular Weight: 554.799
• Mol file: 120595-81-5.mol

Synonyms:(1R,2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

Chemical Property of (1R,2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

There total 1 articles about (1R,2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol 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: 87.0%

1L-5,6-di-O-allyl-1,4-di-O-benzyl-myo-inositol (104873-73-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (1R,2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol (120595-81-5)

Guidance literature:

In pyridine; at 50 ℃; for 16h;

DOI:10.1016/S0040-4039(00)82387-4

Reference yield: 78.0%

benzyl bromide (100-39-0) + (1R,2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol (120595-81-5) → ((1R,2R,3S,4S,5R,6S)-3,4-Bis-allyloxy-2,5,6-tris-benzyloxy-cyclohexyloxy)-tert-butyl-dimethyl-silane (120595-84-8) + ((1S,2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-2,5,6-tris-benzyloxy-cyclohexyloxy)-tert-butyl-dimethyl-silane (120595-84-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)82387-4

Reference yield:

(1R,2S,3R,4S,5R,6R)-3,4-Bis-allyloxy-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol (120595-81-5) → {(1R,2R,3R,4R,5S,6R)-4-Allyloxy-2,3,6-tris-benzyloxy-5-[((E)-propenyl)oxy]-cyclohexyloxy}-tert-butyl-dimethyl-silane

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / NaH / dimethylformamide

2: 1,5-cyclooctadiene-bis(methyldiphenylphosphine)iridium hexafluorophosphate / 1,2-dichloro-ethane

With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; sodium hydride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)82387-4

upstream raw materials:

1L-5,6-di-O-allyl-1,4-di-O-benzyl-myo-inositol

tert-butyldimethylsilyl chloride

Downstream raw materials:

((1R,2R,3S,4S,5R,6S)-3,4-Bis-allyloxy-2,5,6-tris-benzyloxy-cyclohexyloxy)-tert-butyl-dimethyl-silane

((1S,2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-2,5,6-tris-benzyloxy-cyclohexyloxy)-tert-butyl-dimethyl-silane

(1R,2S,3R,4S,5S,6R)-3,4-Bis-allyloxy-2,5,6-tris-benzyloxy-cyclohexanol