139356-35-7

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 2041-15-8 1,3,5-cyclohexanetriol 
• 77-95-2 D-(-)-quinic acid 
• 191916-39-9 methyl (-)-quinate 
• 135711-62-5 methyl quinicate 
• 6973-02-0 (3R)-3r,4c,5t-trihydroxy-cyclohexane-c-carboxylic acid methyl ester 
• 262594-22-9 methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate 
• 101906-39-2 Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate 
• 40983-58-2 methyl shikimate 
• 138-59-0 shikimic acid 
• 139356-33-5 (3S,5S)-3,5-bis[(tert-butyl)dimethylsilyloxy]-1-hydroxycyclohexane-1-carboxylic acid methyl ester 
• 388569-30-0 2-[3,5-di(tert-butyldimethylsilyloxy)cyclohexyloxy]tetrahydro-2H-pyran 

Downstream Products

• 1326758-33-1 C₂₀H₄₂O₃Si₂ 
• 1326319-25-8 C₂₀H₄₂O₃Si₂ 
• 1326319-26-9 C₈H₁₄O₃ 
• 1326319-31-6 C₁₄H₁₆O₃Se 
• 1326319-35-0 C₁₄H₂₀O₄ 
• 1326319-43-0 C₁₇H₂₂N₂O₃ 
• 956634-47-2 N-phenyl-4-tert-butyldimethylsiloxy-L-proline 
• 4096-20-2 N-phenyl piperidine 
• 199613-48-4 5-tert-butyl-dimethylsilyloxy-(5S)-2-cyclohexenone 
• 108-95-2 phenol 
• 139356-36-8 [(3R,5R)-3,5-bis-(tert-butyldimethylsilyloxy)cyclohexylidene]acetic acid ethyl ester 
• 408535-68-2 (3S,5S)-3,5-bis-t-butyldimethylsilyloxy-2-bromo-1-cyclohexanone 

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

Enzymatic Desymmetrization of 19-nor-Vitamin D3 A-Ring Synthon Precursor: Synthesis, Structure Elucidation, and Biological Activity of 1α,25-Dihydroxy-3-epi-19-nor-vitamin D3 and 1β,25-Dihydroxy-19-nor-vitamin D3

In a search for novel vitamin D derivatives of potential therapeutic value, structurally simple but synthetically challenging A-ring epimers of the 19-nor-Calcitriol [19-nor-1α,25-(OH)2-D3] at C1 and C3 were efficiently synthesized. Both analogues (1-epi- and 3-epi-19-nor-Calcitriol) were obtained through a convergent synthesis starting from cis,cis-1,3,5-cyclohexanetriol and the protected 25-hydroxy Grundmann′s ketone. After Julia-Kocienski coupling of the corresponding C,D-ring/side chain sulfone fragment with the A-ring ketone moiety, both vitamin D analogues were isolated. The critical point was how to determine the structural configuration of both diastereoisomers since similar 1H NMR spectra were observed. For that, a biocatalytic approach was crucial in the synthesis of orthogonally protected derivatives. NMR spectroscopy allows the unambiguous identification of these compounds and as a result the structural elucidation of the desired vitamin D diastereomeric analogues. Affinity studies demonstrated that these 1,25-19-nor analogues have a very low affinity for the vitamin D receptor compared with 1α,25-dihydroxyvitamin D3 or 1α,25-dihydroxy-19-nor-vitamin D3. In addition, these analogues have a lower binding affinity for the human vitamin D binding protein than the natural hormone. In vitro cell culture studies revealed that synthesized analogues were less active than 1α,25-dihydroxyvitamin D3 in inhibiting cell proliferation. (Figure presented.).

Preparation method of paricalcitol intermediate

The invention discloses a preparation method of a paricalcitol intermediate, which includes the following steps: (1) shikimic acid is esterified; (2) hydroxyl groups at sites 3 and 5 are selectively protected; (3) hydroxyl group at site 4 is protected by

Synthesis of diastereomers of 1,3-cis-25-dihydroxy-19-norvitamin D3

1β,3β,25-Dihydroxy-19-norvitamin D3 (4a) and 1α,3α,25-dihydroxy-19-norvitamin D3 (4b) were synthesized by employing a new A-ring synthon, (1R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-oxocyclohexyl benzoate (19), which was derived from D-(-)-quinic acid in 12 steps. The A-ring was coupled with the circular dichroism (CD) ring by means of Julia-Kocienski olefination to construct the diene unit. The structures of the products were confirmed by 1H-NMR and nuclear Overhauser effect (NOE) experiments.

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.

A mild and catalyst-free aromatization using dihydroxylcyclohexanone derivatives as phenyl sources: A new approach to anilines

A new and efficient protocol for the preparation of N-substituted anilines via an aromatization reaction was developed. 3,5-Dihydroxylcyclohexanone derivatives were used as the sources of the phenyl group and reacted smoothly with primary or secondary amines under mild conditions in the absence of metal catalyst and strong base. A variety of N-substituted anilines were prepared by this method with excellent yields up to 99%. The results indicate that this reaction begins with a nucleophilic addition.

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

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.

ENANTIOTOPOSELECTIVE PLE-CATALYZED HYDROLYSIS OF CIS-5-SUBSTITUTED-1,3-DIACYLOXYCYCLOHEXANES. PREPARATION OF SOME USEFUL CHIRAL BUILDING BLOCKS

PLE-catalyzed hydrolysis of prochiral cis-5-benzyloxymethyl-1,3-diacetoxycyclohexane and cis-5-benzyloxy-1,3-diacetoxycyclohexane proceeds with high enantiotoposelectivity.The preparation of some useful chiral building blocks is described.