(3R,5R)-3,5-bis-[(t-butyldimethylsilyl)oxy]-4-methylene-cyclohexanol benzyl ether

Base Information

• Chemical Name: (3R,5R)-3,5-bis-[(t-butyldimethylsilyl)oxy]-4-methylene-cyclohexanol benzyl ether
• CAS No.: 681433-63-6
• Molecular Formula: C₂₆H₄₆O₃Si₂
• Molecular Weight: 462.82
• Mol file: 681433-63-6.mol

Synonyms:(3R,5R)-3,5-bis-[(t-butyldimethylsilyl)oxy]-4-methylene-cyclohexanol benzyl ether

Chemical Property of (3R,5R)-3,5-bis-[(t-butyldimethylsilyl)oxy]-4-methylene-cyclohexanol benzyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-3,5-bis-[(t-butyldimethylsilyl)oxy]-4-methylene-cyclohexanol benzyl ether

There total 5 articles about (3R,5R)-3,5-bis-[(t-butyldimethylsilyl)oxy]-4-methylene-cyclohexanol benzyl ether 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: 98.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (2R,6R)-2,6-bis-[(tert-butyldimethylsilyl)oxy]-4-(benzyloxy)cyclohexanone (681433-62-5) → (3R,5R)-3,5-bis-[(t-butyldimethylsilyl)oxy]-4-methylene-cyclohexanol benzyl ether (681433-63-6)

Guidance literature:

With n-butyllithium;

DOI:10.1016/j.bmcl.2004.12.090

Reference yield:

benzyl bromide (100-39-0) → (3R,5R)-3,5-bis-[(t-butyldimethylsilyl)oxy]-4-methylene-cyclohexanol benzyl ether (681433-63-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / aq. AcOH / tetrahydrofuran

2: 100 percent / DMSO; (COCl)2

3: 98 percent / nBuLi

With n-butyllithium; oxalyl dichloride; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; 3: Swern oxidation / 4: Wittig reaction;

DOI:10.1016/j.bmcl.2004.12.090

Reference yield:

(3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone (141404-09-3) → (3R,5R)-3,5-bis-[(t-butyldimethylsilyl)oxy]-4-methylene-cyclohexanol benzyl ether (681433-63-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / NaBH₄

2: 80 percent / aq. AcOH / tetrahydrofuran

3: 100 percent / DMSO; (COCl)2

4: 98 percent / nBuLi

With sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; 4: Swern oxidation / 5: Wittig reaction;

DOI:10.1016/j.bmcl.2004.12.090

upstream raw materials:

Methyltriphenylphosphonium bromide

(2R,6R)-2,6-bis-[(tert-butyldimethylsilyl)oxy]-4-(benzyloxy)cyclohexanone

benzyl bromide

(3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone