139356-33-5

Usage

Uses

Used in Pharmaceutical Industry:
(3S,5S)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl Ester is used as an intermediate in the synthesis of Vitamin D compounds. Its unique structure and reactivity make it a valuable building block for the development of pharmaceuticals, particularly those related to Vitamin D.
Used in Chemical Research:
Due to its complex structure and chiral nature, (3S,5S)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl Ester can be employed as a research tool in the field of organic chemistry. It may be used to study various aspects of stereochemistry, reaction mechanisms, and the development of new synthetic methods.
Used in Material Science:
The unique properties of (3S,5S)-3,5-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-1-hydroxy-cyclohexanecarboxylic Acid Methyl Ester may also find applications in the field of material science. Its potential use in the development of new materials with specific properties, such as improved stability or reactivity, could be explored.

Upstream product

• 139356-32-4 methyl (1s_n,3R,4s_n,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-[(imidazol-1-ylthiocarbonyl)oxy]-cyclohexanecarboxylate 
• 77-95-2 D-(-)-quinic acid 
• 135711-62-5 methyl quinicate 
• 6973-02-0 (3R)-3r,4c,5t-trihydroxy-cyclohexane-c-carboxylic acid methyl ester 
• 40983-58-2 methyl shikimate 
• 138-59-0 shikimic acid 
• 191916-39-9 methyl (-)-quinate 

Downstream Products

• 139356-34-6 (3S,5S)-3,5-bis[tert-butyl(dimethyl)silyloxy]-1-(hydroxylmethyl)cyclohexanol 
• 262594-22-9 methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate 
• 120056-36-2 methyl (3S,5S)-3,5-dihydroxycyclohex-1-enecarboxylate 
• 262594-23-0 methyl (3S,5R)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-cyclohex-1-enecarboxylate 
• 262594-24-1 methyl (3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-3-[(p-nitrophenylcarbonyl)oxy]cyclohex-1-enecarboxylate 
• 301153-91-3 methyl (3R,5S)-3,5-dihydroxycyclohex-1-enecarboxylate 
• 301153-94-6 (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarbaldehyde 
• 301153-87-7 (3S,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarbaldehyde 
• 301153-83-3 methyl (3S,5R)-5-hydroxy-3-[(p-nitrophenylcarbonyl)oxy]-cyclohex-1-enecarboxylate 
• 301153-89-9 methyl (3R,5R)-5-hydroxy-3-[(p-nitrophenylcarbonyl)oxy]-cyclohex-1-enecarboxylate 
• 301153-95-7 (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynylcyclohex-1-ene 
• 301153-88-8 (3S,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynylcyclohex-1-ene 
• 301153-93-5 (3R,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-hydroxymethylcyclohex-1-ene 
• 301153-86-6 (3S,5S)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-hydroxymethylcyclohex-1-ene 

Relevant academic research and scientific papers

Economical Process for Preparation of the 19-nor A Ring of Paricalcitol from (-)-Shikimic Acid

An economical and efficient means of preparing the 19-nor A ring, a key precursor of the vitamin D receptor (VDR) activator Paricalcitol, is here described. This process begins with commercially available (-)-shikimic acid and was easily scaled up to kilo

AMINO QUINOLINE DERIVATIVES INHIBITORS OF HCV

A compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein the substituents are defined herein, and methods of treating HCV infection in a patient are disclosed.

1-DEOXY ANALOGS OF VITAMIN D-RELATED COMPOUNDS

This present disclosure is directed to novel prodrugs of activated vitamin D3 compounds. The prodrugs can be designed to have one or more beneficial properties, such as selective inhibition of the enzyme CYP24, low calcemic activity, and anti-proliferativ

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

6-s-cis locked analogues of the steroid hormone 1α,25-dihydroxyvitamin D3. Synthesis of novel A-ring stereoisomeric 1,25-dihydroxy-3-epi-19-nor-previtamin D3 derivatives

Efficient syntheses of A-ring synthons 24 and 32 are described from hydroxy ester 16, which is easily available on a preparative scale from (-)-quinic acid. Key features of the syntheses were (a) the ability to selectively perform desilylations in the presence of p-nitrobenzoate esters and (b) the excellent yield and complete stereospecificity with which the configuration of alcohols 16, 18, and 26 could be inverted under Mitsunobu conditions. Thus, A-ring synthons 24 and 32 were both prepared in 35-38% yield (eight steps) from the common precursor 16. The coupling of A-ring synthons 24 and 32 with the appropriate CD-ring/side chain fragment 7 provides access to novel 6-s-cis locked analogues of steroid hormone 1α,25-dihydroxyvitamin D3: 1α,25-dihydroxy-3-epi-19-nor-previtamin D3 (37) and 1β,25-dihydroxy-3-epi-19-nor-previtamin D3 (38), which are unable to undergo rearrangement to the respective vitamin D form by virtue of the absence of the C-19 methyl group. Compounds 37 and 38 can be used as tools for studying the genomic and nongenomic mechanisms of action of the previtamin form of the hormone 1α,25-dihydroxyvitamin D3.

Synthesis of two 6-s-cis locked stereoisomeric analogues of the steroid hormone 1α,25-dihydroxyvitamin D3: 1 α,25-dihydroxy-19-nor-previtamin D3 and 1β,25-dihydroxy- 19-nor-previtamin D3

An efficient synthesis of A-ring precursors 8 and 9 from inexpensive commercially available (-)-quinic acid has been developed. A-Ring synthon 8 has been obtained through a short sequence (eight steps) in high overall yield (30%). One key step in the synt

Novel synthesis of 19-nor-vitamin D compounds

1α,25-Dihydroxy-19-nor-vitamin D3 was prepared efficiently in a convergent synthesis starting with (-)-quinic acid and a ketone of the Windaus-Grundmann type.