262594-22-9

Upstream product

• 139356-33-5 (3S,5S)-3,5-bis[(tert-butyl)dimethylsilyloxy]-1-hydroxycyclohexane-1-carboxylic acid methyl ester 
• 191916-39-9 methyl (-)-quinate 
• 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 
• 77-95-2 D-(-)-quinic acid 
• 139356-32-4 methyl (1s_n,3R,4s_n,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-[(imidazol-1-ylthiocarbonyl)oxy]-cyclohexanecarboxylate 
• 135711-62-5 methyl quinicate 

Downstream Products

• 139356-35-7 3,5-di-(tert-butyl-dimethylsilyloxy)-(3S,5S)-cyclohexan-1-one 
• 139356-37-9 [(3R,5R)-3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidene]-ethanol 
• 139356-38-0 ((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane) 
• 139356-39-1 (1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane 
• 139356-34-6 (3S,5S)-3,5-bis[tert-butyl(dimethyl)silyloxy]-1-(hydroxylmethyl)cyclohexanol 
• 262594-19-4 (1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynylcyclohex-4-ene-1,3-diol 
• 262594-20-7 (1R,3R)-5-[(1R,3aR,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-ylethynyl]-cyclohex-4-ene-1,3-diol 
• 262594-26-3 (3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enecarboxylic acid methyl ester 
• 262594-21-8 3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynylcyclohex-1-ene 
• 262594-25-2 (3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 144699-06-9 (1R,3S)-5-[(Z)-2-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]cyclohex-4-ene-1,3-diol 
• 144699-11-6 (3S,5S)-3,5-bis(tert-butyldimethylsilyloxy)cyclohex-1-enecarbaldehyde 
• 144699-08-1 3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynylcyclohex-1-ene 
• 445029-09-4 methyl (3S,5R)-3,5-dihydroxycyclohex-1-enecarboxylate 

Relevant academic research and scientific papers

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.

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 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