meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol

Base Information

• Chemical Name: meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol
• CAS No.: 134522-14-8
• Molecular Formula: C₃₈H₄₈O₄Si₂
• Molecular Weight: 624.968
• Mol file: 134522-14-8.mol

Synonyms:meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol

Chemical Property of meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol

There total 6 articles about meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol 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: 73.0%

3,6-bis(tert-butyldiphenylsilyloxy)cyclohex-1-ene → meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol (134522-14-8)

Guidance literature:

With ruthenium trichloride; sodium periodate; In water; ethyl acetate; acetonitrile; at 0 ℃; for 0.0166667h;

DOI:10.1021/jo0259111

Reference yield:

(1R,2R,3S,6R)-3,6-Bis-(tert-butyl-diphenyl-silanyloxy)-cyclohexane-1,2-diol (134341-47-2,134522-14-8) → meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol (134522-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) 98 percent periodic acid, 2) molecular sieves / 1) THF, 30 min, 2) THF, 2 h

2: SmI₂ / tetrahydrofuran / 1) -78 deg C, 1 h, 2) to 25 deg C, 2 h

With molecular sieve; samarium diiodide; periodic acid; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)92024-0

Reference yield:

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial (134341-56-3) → meso-(1R,2S,3S,6R)-3,6-bis(tert-butyldiphenylsilyloxy)cyclohexane-1,2-diol (134522-14-8)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; Yield given; 1) -78 deg C, 1 h, 2) to 25 deg C, 2 h;

DOI:10.1016/S0040-4039(00)92024-0

upstream raw materials:

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial

(1R,2R,3S,6R)-3,6-Bis-(tert-butyl-diphenyl-silanyloxy)-cyclohexane-1,2-diol

Downstream raw materials:

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial

(1S,2R,3S,6R)-3,6-Bis-(tert-butyl-diphenyl-silanyloxy)-cyclohexane-1,2-diol

(Z)-(4S,7R)-4,8-bis(tert-butyldiphenylsilyloxy)-7-hydroxyocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

(Z)-(4S,7R)-4,7-bis(tert-butyldiphenylsilyloxy)-8-oxoocta-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester