1583259-86-2

Basic information

• Product Name: 5-benzyloxy-1-hydroxy-3-hydroxy-2-tert-butyl-β-D-arabinose
• CAS NO: 1583259-86-2
• Molecular Weight: 280.364
• Mol File: 1583259-86-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-benzyloxy-1-hydroxy-3-hydroxy-2-tert-butyl-β-D-arabinose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-benzyloxy-1-hydroxy-3-hydroxy-2-tert-butyl-β-D-arabinose(1583259-86-2)
• EPA Substance Registry System: 5-benzyloxy-1-hydroxy-3-hydroxy-2-tert-butyl-β-D-arabinose(1583259-86-2)

Safety Data

• Hazardous Substances Data: 1583259-86-2(Hazardous Substances Data)

Upstream product

• 60498-66-0 isopropyl 3,3-dimethylbutanoate 
• 1070-83-3 tert-Butylacetic acid 
• 1583259-23-7 (E)-((1-isopropoxy-3,3-dimethylbut-1-en-1-yl)oxy)trimethylsilane 
• 1583259-07-7 (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal 
• 1583259-42-0 (2S,3S,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-tert-butyl-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate 
• 1583259-62-4 5-benzyloxy-3-hydroxy-2-tert-butyl-D-arabinolactone 
• 19790-60-4 3-Benzyloxypropanal 
• 100-39-0 benzyl bromide 
• 4799-68-2 3-benzyloxypropan-1-ol 

Relevant articles and documents

A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir

An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.