135711-62-5

Basic information

• Product Name: (1α,3R,4α,5R)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester
• Synonyms: (1α,3R,4α,5R)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester;[1R-(1α,3α,4α,5β)]-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: 434.71488
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 135711-62-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: 82-82.5 °C(Solv: hexane (110-54-3))
• Boiling Point: 430.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.02±0.1 g/cm3(Predicted)
• Solubility: CDCl3, CD3OD
• PKA: 12.11±0.70(Predicted)
• CAS DataBase Reference: (1α,3R,4α,5R)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1α,3R,4α,5R)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester(135711-62-5)
• EPA Substance Registry System: (1α,3R,4α,5R)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester(135711-62-5)

Safety Data

• Hazardous Substances Data: 135711-62-5(Hazardous Substances Data)

Usage

Description

(1α,3R,4α,5R)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester is a complex organic compound with a unique molecular structure. It is characterized by its multiple stereocenters and functional groups, which contribute to its specific properties and potential applications.

Uses

Used in Pharmaceutical Industry:
(1α,3R,4α,5R)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester is used as an intermediate in the synthesis of Vitamin D compounds for the pharmaceutical industry. Its unique structure plays a crucial role in the preparation of these essential nutrients, which are vital for maintaining healthy bones and immune system function.
Used in Chemical Research:
(1α,3R,4α,5R)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic Acid Methyl Ester may also be utilized in chemical research as a model for studying the effects of stereochemistry on molecular properties and reactivity. Its complex structure provides an opportunity for researchers to explore various aspects of organic chemistry, including stereoselective synthesis and the influence of functional groups on molecular behavior.

Upstream product

• 191916-39-9 methyl (-)-quinate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 77-95-2 D-(-)-quinic acid 

Downstream Products

• 139356-36-8 [(3R,5R)-3,5-bis-(tert-butyldimethylsilyloxy)cyclohexylidene]acetic acid ethyl ester 
• 139356-32-4 methyl (1s_n,3R,4s_n,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-[(imidazol-1-ylthiocarbonyl)oxy]-cyclohexanecarboxylate 
• 213250-58-9 (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-oxocyclohexanecarboxylic acid methyl ester 
• 901129-88-2 methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate 
• 901129-91-7 methyl 4-O-methanesulfonylquinate 
• 608535-10-0 (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-propylcyclohexanone 
• 608535-09-7 (3R,5R)-4-allyl-3,5-bis[(tert-butyldimethylsilyl)oxy]cyclohexanone 
• 608535-11-1 (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-(3-hydroxypropyl)cyclohexanone 
• 608535-12-2 (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-[3-(tert-butyldimethylsilyloxy)propyl]cyclohexanone 

Relevant articles and documents

Efficient and convergent coupling route for the short-step synthesis of enantiopure 2α- and 2β-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues

Novel efficient synthesis of several enantio-pure 2-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues through radical introduction of 2-alkyl chain and C5-C6 position coupling using Julia-type olefination as key steps w

Synthesis, Structure, and Tandem Mass Spectrometric Characterization of the Diastereomers of Quinic Acid

(-)-Quinic acid possess eight possible stereoisomers, which occur both naturally and as products of thermal food processing. In this contribution, we have selectively synthesized four isomers, namely, epi-quinic acid, muco-quinic acid, cis-quinic acid, and scyllo-quinic acid, to develop a tandem LC-MS method identifying all stereoisomeric quinic acids. Four derivatives have been unambiguously characterized by single-crystal X-ray crystallography. The missing diastereomers of quinic acid were obtained by nonselective isomerization of (-)-quinic acid using acetic acid/concentrated H2SO4 allowing chromatographic separation and assignment of all diastereomers of quinic acid. We report for the first time that a full set of stereoisomers are reliably distinguishable on the basis of their tandem mass spectrometric fragment spectra as well as their elution order. A rationale for characteristic fragmentation mechanisms is proposed. In this study, we also observed that muco-quinic acid, scyllo-quinic acid, and epi-quinic acid are present in hydrolyzed Guatemalan roasted coffee sample as possible products of roasting.

HYBRID MOLECULES HAVING MIXED VITAMIN D RECEPTOR AGONISM AND HISTONE DEACETYLASE INHIBITORY PROPERTIES

Hybrid molecules comprising a vitamin D receptor agonist moiety and an HDAC inhibitor moiety are described herein The HDAC inhibitor moiety can be modelled after an HDAC inhibitor selected from the group consisting of tπchostatm A, sodium butyrate, valpro