112574-58-0

Basic information

• Product Name: (1S,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane
• Synonyms: (1S,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane
• CAS NO: 112574-58-0
• Molecular Weight: 426.628
• Mol File: 112574-58-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1S,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane(112574-58-0)
• EPA Substance Registry System: (1S,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane(112574-58-0)

Safety Data

• Hazardous Substances Data: 112574-58-0(Hazardous Substances Data)

Upstream product

• 112543-74-5 (3aS,6aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one 
• 112543-74-5 (1S,2S,4S)-4-(t-butyldiphenylsilyloxymethyl)-1,2-isopropylidenedioxy-3-cyclopentanone 
• 112543-75-6 (3aR,4S,5S,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 105285-29-8 (1S,2S,3S,4S)-2-acetoxy-1-(acetoxymethyl)-3,4-(isopropylidenedioxy)cyclopentane 
• 112543-73-4 (1S,2S,3S,4S)-1-<((tert-butyldiphenylsilyl)-oxy)methyl>-2,3-(isopropylidenedioxy)cyclopenetane 

Downstream Products

• 112543-76-7 (1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-4-hydroxy-2,3-(isopropylidenedioxy)cyclopentane 
• 112543-73-4 (1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane 
• 113299-31-3 (1S,2S,3R,4R)-(+)-4-(Hydroxymethyl)cyclopentane-1,2,3-triol 
• 85026-59-1 (-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane 
• 112543-78-9 (1R,2R,3S,4R)-4-azido-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2,3-(isopropylidenedioxy)cyclopentane 
• 112543-77-8 (1R,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2,3-(isopropylidenedioxy)-4-<(methylsulfonyl)oxy>cyclopentane 
• 113299-30-2 4a-carba-β-L-lyxofuranose 

Relevant articles and documents

Transformation of D-Erythrose to Some Pseudoaldopentofuranoses. Syntheses of (1S,2R,3S,4S)-, (1R,2R,3S,4S)-, and (1R,2S,3S,4S)-2,3,4-Trihyroxy-1-(hydroxymethyl)cyclopentanes and (1R,2S,3R,4R)-2,3-Dihydroxy-4-(hydroxymethyl)-1-cyclopentanamine

Sodium borohydride reduction of (1S,3S,4S)-1--3,4-(isopropylidenedioxy)-2-cyclopentanone (11), which was prepared from D-erythrose, proceeds exlusively from the β-face to provide 2R-hydroxyl derivative 12.Compound 12 is a derivative of carbocyclic analogue of β-L-lyxofuranose.Silica gel promoted configurational inversion at the branched carbon in 11 followed by sodium borohydride reduction provides 1R,2R diastereomer 17 and 12 a 2.8:1 ratio.The former is a protected form of carboxylic α-D-ribofuranose.Replacement of the mesyloxy group in 23, which was derived from 17, by a hydroxyl group in a SN2 fashion and deprotection of the product followed by acetylation gave a derivative of carbocyclic α-D-xylofuranose 24.Compound 17 was also converted to compound 7, a key intermediate for the synthesis of the carboxylic nucleoside antibiotic (-)-aristeromycin (1), via a SN2 replacement of the mesyloxy group in 26 by an azide group.