541513-63-7

Basic information

• Product Name: (2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyric acid benzyl ester
• Synonyms: (2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyric acid benzyl ester
• CAS NO: 541513-63-7
• Molecular Weight: 308.375
• Mol File: 541513-63-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyric acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyric acid benzyl ester(541513-63-7)
• EPA Substance Registry System: (2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyric acid benzyl ester(541513-63-7)

Safety Data

• Hazardous Substances Data: 541513-63-7(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 541513-60-4 (2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyric acid 
• 541513-52-4 (4R)-4-benzyl-3-{(2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyryl}oxazolidin-2-one 
• 95422-24-5 methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate 
• 32233-44-6 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde 

Downstream Products

• 541513-95-5 (2R,3S,5S)-6-bis(benzyloxy)phosphoryloxy-2-methyl-3,5-bis(tetrahydropyran-2-yloxy)hexanoic acid benzyl ester 
• 541513-79-5 (2R,3S,5S)-3,5-diacetoxy-6-bis(benzyloxy)phosphoryloxy-2-methylhexanoic acid benzyl ester 
• 541513-71-7 (2R,3S,5S)-6-[bis(benzyloxy)phosphoryloxy]-3,5-dihydroxy-2-methylhexanoic acid benzyl ester 
• 541513-67-1 (2R,3S,5S)-3,5,6-trihydroxy-2-methylhexanoic acid benzyl ester 

Relevant articles and documents

Synthesis of (R)-2-methyl-4-deoxy and (R)-2-methyl-4,5-dideoxy analogues of 6-phosphogluconate as potential inhibitors of 6-phosphogluconate dehydrogenase.

The synthesis of (2R)-2-methyl-4,5-dideoxy and (2R)-2-methyl-4-deoxy analogues of 6-phosphogluconate is described. The synthetic strategy relies on the Evans aldol reaction for the installation of the chiral centres in the 2- and 3-positions. The selective phosphorylation at the primary alcohol function of (2R,3S)-3,6-dihydroxy-2-methylhexanoic acid benzyl ester (5) and (2R,3S,5S)-3,5,6-trihydroxy-2-methylhexanoic acid benzyl ester (20) was achieved with dibenzyl phosphochloridate and dibenzyl phosphoiodinate respectively, working at low temperature. (2R,3S)-3-Hydroxy-2-methyl-6-phosphonoxyhexanoic acid (9) was obtained in 25% overall yield from 4-benzyloxybutanol and (2R,3S,5S)-3,5-dihydroxy-2-methyl-6-phosphonoxyhexanoic acid (28) in 10% overall yield from L-malic acid.