(1a,3R,4a,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester

Base Information

• Chemical Name: (1a,3R,4a,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester
• CAS No.: 135711-62-5
• Molecular Formula: C20H42O6Si2
• Molecular Weight: 434.721
• DSSTox Substance ID: DTXSID30472958
• Mol file: 135711-62-5.mol

Synonyms:135711-62-5;(1a,3R,4a,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester;methyl (3R,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylate;SCHEMBL9010539;DTXSID30472958;DBNMGEIRSATOJZ-SSWGIJEZSA-N;(1|A,3R,4|A,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester;(1alpha,3R,4alpha,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Aci

Chemical Property of (1a,3R,4a,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester

Chemical Property:

• Melting Point: 82-82.5 °C(Solv: hexane (110-54-3))
• Boiling Point: 430.2±45.0 °C(Predicted)
• PKA: 12.11±0.70(Predicted)
• PSA: 85.22000
• Density: 1.02±0.1 g/cm3(Predicted)
• LogP: 3.82600
• Solubility.: CDCl3, CD3OD
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 434.25199212
• Heavy Atom Count: 28
• Complexity: 524

Purity/Quality:

98% ^*data from raw suppliers

(1α,3R,4α,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC(CC(C1O)O[Si](C)(C)C(C)(C)C)(C(=O)OC)O
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@@H]1CC(C[C@H](C1O)O[Si](C)(C)C(C)(C)C)(C(=O)OC)O
• Uses: (1α,3R,4α,5R)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester is used in the preparation of Vitamin D compounds.

Technology Process of (1a,3R,4a,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester

There total 6 articles about (1a,3R,4a,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,4-dihydroxy-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: 75.0%

methyl (-)-quinate (191916-39-9) + tert-butyldimethylsilyl chloride (18162-48-6) → methyl quinicate (135711-62-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 18h;

DOI:10.1021/jo0606249

Reference yield:

methyl (-)-quinate (191916-39-9) + tert-butyldimethylsilyl chloride (18162-48-6) → C14H28O6Si + methyl quinicate (135711-62-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 - 40 ℃; for 20.5h;

Reference yield:

D-(-)-quinic acid (77-95-2) → methyl quinicate (135711-62-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / HCl / 6 h / 60 °C

2: 75 percent / Et₃N / dimethylformamide / 18 h / 0 - 20 °C

With hydrogenchloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jo0606249

upstream raw materials:

methyl (-)-quinate

tert-butyldimethylsilyl chloride

D-(-)-quinic acid

Downstream raw materials:

p-Toluic acid

C₃₆H₆₆O₂Si₂

C₃₄H₆₂O₂Si₂

C₃₅H₆₄O₂Si₂

Refernces

• 1、 -. "P-TOLUIC ACID PRODUCING METHOD". Paragraph 0045. . Retrieved 2018/11/02.
• 2、 -. "1-DEOXY ANALOGS OF VITAMIN D-RELATED COMPOUNDS". Page/Page column 59-60. . Retrieved 2011/08/04.