443127-32-0

Basic information

• Product Name: 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxitol
• Synonyms: 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxitol
• CAS NO: 443127-32-0
• Molecular Weight: 622.993
• Mol File: 443127-32-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxitol(443127-32-0)
• EPA Substance Registry System: 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxitol(443127-32-0)

Safety Data

• Hazardous Substances Data: 443127-32-0(Hazardous Substances Data)

Upstream product

• 443127-29-5 5-O-triphenylmethyl-L-lyxono-γ-lactone 
• 104196-15-8 lyxonic acid-1,4-lactone 
• 76-83-5 trityl chloride 
• 443127-30-8 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxono-γ-lactone 

Downstream Products

• 443127-34-2 2,3-bis-O-tert-butyldimethylsilyl-1,4-bis-O-methanesulfonyl-5-O-triphenylmethyl-L-lyxitol 

Relevant articles and documents

Toward a general strategy for the synthesis of 3,4-dihydroxyprolines from pentose sugars

A general strategy is proposed, wherein a pentose sugar γ-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-D-2,3-cis-3, 4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-cis-3, 4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl- 3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.