(3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl Ester

Base Information

• Chemical Name: (3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl Ester
• CAS No.: 139356-33-5
• Molecular Formula: C₂₀H₄₂O₅Si₂
• Molecular Weight: 418.721
• DSSTox Substance ID: DTXSID20473919
• Nikkaji Number: J1.233.290D
• Mol file: 139356-33-5.mol

Synonyms:139356-33-5;methyl (3S,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-1-hydroxycyclohexane-1-carboxylate;(3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl Ester;CID 11825917;Cyclohexanecarboxylic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-, methyl ester, (3S,5S)-;SCHEMBL13531906;DTXSID20473919;AKOS025401015;A886039;(3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl E

Chemical Property of (3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl Ester

Chemical Property:

• Boiling Point: 401.3±45.0 °C(Predicted)
• PKA: 12.37±0.60(Predicted)
• Density: 0.98±0.1 g/cm3(Predicted)
• Solubility.: CDCl3, CD3OD
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 418.25707750
• Heavy Atom Count: 27
• Complexity: 496

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC(CC(C1)(C(=O)OC)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)(C(=O)OC)O)O[Si](C)(C)C(C)(C)C
• Uses: (3S,5S)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl Ester is used in the preparation of Vitamin D compounds.

Technology Process of (3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl Ester

There total 12 articles about (3S,5S)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl Ester 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: 100.0%

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)dimethylsilyloxy]-1-hydroxycyclohexane-1-carboxylic acid methyl ester (139356-33-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 3h; Inert atmosphere; Reflux;

Reference yield: 78.0%

(3R,5R)-3,5-bis[(tert-butyl)dimethylsilyloxy]cyclohexane-1-carboxylic acid methyl ester → (3S,5S)-3,5-bis[(tert-butyl)dimethylsilyloxy]-1-hydroxycyclohexane-1-carboxylic acid methyl ester (139356-33-5)

Guidance literature:

(3R,5R)-3,5-bis[(tert-butyl)dimethylsilyloxy]cyclohexane-1-carboxylic acid methyl ester; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -70 - -65 ℃; for 1h; Inert atmosphere; Large scale;

With N-(benzenesulfonyl)-3-phenyloxaziridine; In tetrahydrofuran; toluene; at -70 - -65 ℃; for 3h; Inert atmosphere; Large scale;

DOI:10.1021/acs.oprd.9b00209

Reference yield: 57.0%

D-(-)-quinic acid (77-95-2) → (3S,5S)-3,5-bis[(tert-butyl)dimethylsilyloxy]-1-hydroxycyclohexane-1-carboxylic acid methyl ester (139356-33-5)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(99)02152-8

upstream raw materials:

methyl (1s_n,3R,4s_n,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-[(imidazol-1-ylthiocarbonyl)oxy]-cyclohexanecarboxylate

D-(-)-quinic acid

methyl (-)-quinate

methyl quinicate

Refernces

• 1、 -. "AMINO QUINOLINE DERIVATIVES INHIBITORS OF HCV". Page/Page column 124; 125. . Retrieved 2013/07/05.
• 2、 -. "HYBRID MOLECULES HAVING MIXED VITAMIN D RECEPTOR AGONISM AND HISTONE DEACETYLASE INHIBITORY PROPERTIES". Page/Page column 23; 40. . Retrieved 2008/06/13.