187851-96-3

Upstream product

• 187851-95-2 (4-methoxyphenyl)methyl hex-5-enoate 
• 824-94-2 p-methoxybenzyl chloride 
• 1577-22-6 5-hexenoic acid 

Downstream Products

• 187851-97-4 (4-methoxyphenyl)methyl (R)-6-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhexanoate 
• 128726-47-6 (+)-(S)-6-hydroxymethyl-2-piperidinone 
• 209257-75-0 (S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one 
• 213533-01-8 (S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-hexanoic acid 4-methoxy-benzyl ester 
• 213533-00-7 (R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methanesulfonyloxy-hexanoic acid 4-methoxy-benzyl ester 
• 175398-33-1 (R)-6-<<(tert-butyldiphenylsilyl)oxy>methyl>-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 187851-99-6 (3RS,6R)-6-(hydroxymethyl)-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 187851-98-5 (3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Practical asymmetric synthesis of both enantiomers of 6-(hydroxymethyl)piperidin-2-one

A practical asymmetric synthesis of both enantiomers of 6 (hydroxymethyl)piperidin-2-one 1 is described. Asymmetric dihydroxylation (AD) of alkenyl ester 2 using the (DHQ)2AQN ligand provides diol (5S)-3 in ≤95% ee after recrystallisation. This diol can subsequently be transformed into (6R)-1 using a five step reaction sequence. By employing (DHQD)2AQN [1,4-bis(dihydroquininyl)anthraquinone] in the initial AD reaction, (6S)-1 can be prepared in an analogous fashion.

Determination of the relative and absolute stereochemistry of fostriecin (CI-920)

The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D 1H-1H NMR NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide 4 revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.