172471-74-8

Basic information

• Product Name: Butanoic acid, 2-hydroxy-4-(phenylmethoxy)-, (S)-
• CAS NO: 172471-74-8
• Molecular Formula: C11H14O4
• Molecular Weight: 210.23
• Mol File: 172471-74-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 2-hydroxy-4-(phenylmethoxy)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 2-hydroxy-4-(phenylmethoxy)-, (S)-(172471-74-8)
• EPA Substance Registry System: Butanoic acid, 2-hydroxy-4-(phenylmethoxy)-, (S)-(172471-74-8)

Safety Data

• Hazardous Substances Data: 172471-74-8(Hazardous Substances Data)

Upstream product

• 616876-80-3 (S)-2-Phenyl-[1,3]dioxane-4-carboxylic acid (S)-2-phenyl-[1,3]dioxan-4-ylmethyl ester 
• 286856-62-0 (S)-2-Phenyl-[1,3]dioxane-4-carboxylic acid tert-butyl ester 
• 256390-84-8 (S)-4-(hydroxymethyl)-2-phenyl-1,3-dioxane 
• 59408-74-1 (S)-2-((tert-butoxy)carbonylamino)-4-(phenylmethoxy)butyric acid 
• 178680-93-8 t-butyl 4-O-benzyl-3-deoxy-L-tetronate 

Downstream Products

• 182273-61-6 C₅₃H₇₂N₂O₁₃Si 

Relevant articles and documents

New N-acylating reagents derived from 3-deoxy-L-glycero-tetronic acid

Commercially available N-Boc-4-O-benzyl-L-homoserine was treated with trifluoroacetic acid and the corresponding, N-deprotected derivative was submitted to deamination to give 4-O-benzyl-3-deoxy-L-glycero-tetronic acid (5). In another approach to 3-deoxy-L-glycero-tetronic acid protected at position 4, the carboxylic groups in L-malic acid were reduced, and the resulting triol was benzylidenated. Oxidation of the 2,4-O-benzylidene derivative formed with CrO3-pyridine complex in the presence of t-butyl alcohol gave t-butyl 2,4-O-benzylidene-3-deoxy-L-glycero-tetronate (13). The latter was saponified with aqueous sodium hydroxide to give, after Na+ exchange for H+, 2,4-O-benzylidene-3-deoxy-L-glycero-tetronic acid (15). Opening of the acetal ring in 13, followed by hydrolytic cleavage of the t-butyl ester function gave material indistinguishable from 5 obtained in the original way. When tested for their efficiency of N-acylation of derivatives of D-perosamine, both acids 5 and 15 gave the corresponding tetronamido derivatives in high yields.