(3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanemethanol

Base Information

• Chemical Name: (3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanemethanol
• CAS No.: 139356-34-6
• Molecular Formula: C₁₉H₄₂O₄Si₂
• Molecular Weight: 390.711
• DSSTox Substance ID: DTXSID60471232
• Mol file: 139356-34-6.mol

Synonyms:139356-34-6;(3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanemethanol;(3S,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-1-(hydroxymethyl)cyclohexan-1-ol;SCHEMBL3186681;DTXSID60471232

Chemical Property of (3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanemethanol

Chemical Property:

• Solubility.: CDCl3, CD3OD
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 390.26216289
• Heavy Atom Count: 25
• Complexity: 413

Purity/Quality:

98% ^*data from raw suppliers

(3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC(CC(C1)(CO)O)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@H]1C[C@@H](CC(C1)(CO)O)O[Si](C)(C)C(C)(C)C
• Uses: (3S,5S)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1-hydroxy-cyclohexaneMethanol is used in the preparation of Vitamin D compounds.

Technology Process of (3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanemethanol

There total 15 articles about (3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanemethanol 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%

(3S,5S)-3,5-bis[(tert-butyl)dimethylsilyloxy]-1-hydroxycyclohexane-1-carboxylic acid methyl ester (139356-33-5) → (3S,5S)-3,5-bis[tert-butyl(dimethyl)silyloxy]-1-(hydroxylmethyl)cyclohexanol (139356-34-6)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃;

Reference yield: 87.0%

C20H40O5Si2 → (3S,5S)-3,5-bis[tert-butyl(dimethyl)silyloxy]-1-(hydroxylmethyl)cyclohexanol (139356-34-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -78 ℃; for 4h;

Reference yield:

methyl (1sn,3R,4sn,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-[(imidazol-1-ylthiocarbonyl)oxy]-cyclohexanecarboxylate (139356-32-4) → (3S,5S)-3,5-bis[tert-butyl(dimethyl)silyloxy]-1-(hydroxylmethyl)cyclohexanol (139356-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Bu₃SnH, azobisisobutyronitrile (AIBN) / toluene / 2 h / 80 °C

2: 60 percent / DIBAL-H / toluene / 2 h / -78 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; diisobutylaluminium hydride; In toluene;

DOI:10.1016/0040-4039(91)80559-O

upstream raw materials:

(3S,5S)-3,5-bis[(tert-butyl)dimethylsilyloxy]-1-hydroxycyclohexane-1-carboxylic acid methyl ester

D-(-)-quinic acid

methyl (-)-quinate

methyl quinicate

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