116627-67-9

Upstream product

• 927211-53-8 (4R,6S)-4-tert-butyldiphenylsilyloxy-6-(p-tosyloxymethyl)tetrahydropyran-2-one 
• 100636-39-3 methyl 3-carbonyl-5-hexenoate 
• 109462-44-4 (R)-3-hydroxy-5-hexenoic acid methyl ester 
• 119003-49-5 (3R)-(-)-3-hydroxyhex-5-enoic acid 
• 110772-23-1 [(2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-methanol 
• 116627-69-1 (4R,6S)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one 
• 116697-27-9 ((2S,4R)-2-Benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-tert-butyl-diphenyl-silane 
• 116697-28-0 (4R,6S)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ol 
• 91312-53-7 ethyl (3R,5S)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 927211-52-7 (4R,6S)-4-tert-butyldiphenylsilyloxy-6-(hydroxymethyl)tetrahydropyran-2-one 
• 915201-15-9 ethyl (3R,5S)-3-tert-butyldiphenylsilyloxy-5,6-(isopropylidenedioxy)hexanoate 
• 121772-46-1 (3R)-3-hex-5-enoic acid 

Relevant academic research and scientific papers

Synthesis of the chiral side chain of statins - Lactone versus lactol pathway

4-O-Protected (4R,6S)-4-hydroxy-6-(hydroxymethyl)tetrahydropyran-2-ones (3) derived from enantiomerically pure (3R,5S)-3-hydroxy-5,6-(isopropylidenedioxy) hexanoates (2) are frequently considered as pivotal intermediates for the synthesis of pharmacologic

Methyl (3R)-3-Hydroxyhex-5-enoate as a Precursor to Chiral Mevinic Acid Analogues

Baker's yeast reduction of methyl 3-oxohex-5-enoate 14b provides methyl (3R)-3-hydroxyhex-5-enoate 15b with 78percent enantiomeric enrichment.Subsequent seleno- and iodo-lactonization of derived hex-5-enoic acids leads to valerolactones 18, 19, 25 and 26 which are suitable for the subsequent elaboration of a variety of mevinic acid analogues.The absolute configuration of the major enantiomer produced in the initial yeast reduction was determined by correlation with natural (S)-(+)-parasorbic acid 23.

SYNTHESES OF 4(R)-SILYLOXY-6(S)-IODOMETHYL-TETRAHYDROPYRAN-2-ONE AND ITS ENANTIOMER, BUILDING BLOCKS FOR HMG-COA REDUCTASE INHIBITORS

Optically pure 4(R),6(S)-iodolactone 1 was obtained from α-D-(+)-glucose in 17 steps with 17percent overall yield.Its enantiomer 4(S),6(R)-iodolactone 1' was obtained from acetonedicarboxylic acid in 9 steps in 37percent overall yield and with 70percent e

CHIRAL SYNTHONS FOR THE ELABORATION OF MEVINIC ACID ANALOGUES

Baker's yeast reduction of methyl 3-oxo-5-hexenoate (6b) affords the (R)-hydroxy-ester (7b) (76percent ee) wich is converted into the lactones (15) and epoxy-ester (19), synthons of the lactone part of the mevinic acids.