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

Base Information

• Chemical Name: (1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol
• CAS No.: 176380-10-2
• Molecular Formula: C₂₈H₃₀O₄
• Molecular Weight: 430.544
• Mol file: 176380-10-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 53 articles about (1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-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: 96.0%

(1S,4S,5R,6R)-methyl 4,5,6-tris(benzyloxy)-cyclohex-2-enecarboxylate (1261160-14-8) → (1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol (176380-10-2)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; for 0.5h;

DOI:10.1016/j.tetasy.2010.10.010

Reference yield: 87.0%

(2R,3R,4R,5S)-3,4,5-tri(benzyloxy)-2-vinyl-6-hepten-1-ol (844901-87-7) → (1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol (176380-10-2)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane;

DOI:10.1021/jo048459p

Reference yield: 85.0%

tributyl(((1R,4R,5S,6S)-4,5,6-tris(benzyloxy)cyclohex-2-enyloxy)methyl)stannane → (1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol (176380-10-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.joc.6b00616

upstream raw materials:

tri-n-butylstannylmethyl iodide

(-)-(1R,2S,3S,4R)-2,3,4-tribenzyloxy-5-cyclohexene-1-ol

Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester

(2R,3R,4R,5S)-3,4,5-tri(benzyloxy)-2-vinyl-6-hepten-1-ol

Downstream raw materials:

((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

C₂₉H₃₂O₄

cyclophellitol