105265-95-0

Basic information

• Product Name: rac-Carba-β-arabinofuranose
• CAS NO: 105265-95-0
• Molecular Weight: 148.159
• Mol File: 105265-95-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: rac-Carba-β-arabinofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: rac-Carba-β-arabinofuranose(105265-95-0)
• EPA Substance Registry System: rac-Carba-β-arabinofuranose(105265-95-0)

Safety Data

• Hazardous Substances Data: 105265-95-0(Hazardous Substances Data)

Upstream product

• 133491-12-0 (3aS,4S,6R,6aR)-6-Methoxymethoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 115384-58-2 6-<(methoxymethoxy)methyl>-2,2-dimethyl-3aβ,5,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxol-4-one 
• 105265-94-9 (1S,2S,3S,4S)-2,3,4-triacetoxy-1-(acetoxymethyl)cyclopentane 
• 384341-74-6 (1S,2S,3S,4S)-2,3-di-O-(tert-butyldimethylsilanyl)-4-hydroxymethylcyclopentane-1,2,3-triol 
• 127940-37-8 (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one 
• 127940-36-7 (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one 
• 131530-77-3 (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])dihydrofuran-2-one 
• 384341-71-3 (2S,2'S)-2-(tert-butyldimethylsilanyloxy)-(5-oxo-tetrahydrofuran-2-yl)acetaldehyde 
• 384341-88-2 (S)-5-[(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-propyl]-dihydro-furan-2-one 
• 384341-87-1 (S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-dihydro-furan-2-one 
• 384341-72-4 (1S,4R,5S,6S)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one 
• 1410003-52-9 (1S,2R,3S,4S)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol 
• 1410003-58-5 (1S,2R,3S,4S)-1-O-benzyl-4-hydroxymethyl-cyclopentane-1,2,3-triol 
• 105265-91-6 (3aS,6aS)-4-Acetoxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-5,5-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Variable strategy toward carbasugars and relatives. 2. Diversity-based synthesis of β-D-xylo, β-D-ribo, β-L-arabino, and β-L-lyxo 4a-carbafuranoses and (4a-carbafuranosyl)thiols

The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-β-D-xylofuranose, 4a-carba-β-D-ribofuranose, 4a-carba-β-L-arabinofuranose, and 4a-carba-β-L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-β-D-xylofuranosyl)thiol, (4a-carba-β-D-ribofuranosyl)thiol, (4a-carba-β-L-arabinofuranosyl)thiol, and (4a-carba-β-L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.

(R)-2,3-O-Cyclohexylideneglyceraldehyde: A useful template for a simple entry into carbafuranose stereoisomers

(R)-2,3-O-Cyclohexylideneglyceraldehyde 1 provides a simple route for the preparation of carbafuranoses. This has been exemplified by the preparation of 10c and 10d, the derivatives of carba d-xylofuranose and carba-l-arabinofuranose respectively, starting from homoallylic alcohol 2a derived from 1. The key step in this protocol was the intramolecular allylation of 9 promoted by several metals under wet conditions that resulted in the construction of the carbafuranose skeleton of 10. The potential of several metals regarding the efficacy and stereoselectivity of this crucial intramolecular allylation reaction has been studied. The moderate stereoselectivity in all of the successful intramolecular allylations of 9 yielding both d-10c and l-10d as the major products contributed significantly in attaining stereo-divergence in this route. The utility of this route was due to the easy availability of 1, and the operational simplicity as well as scalability of all of the reactions involved.

BIOSYNTHESIS OF ARISTEROMYCIN: EVIDENCE FOR THE INTERMEDIACY OF A 4β-HYDROXYMETHYL-1α,2α,3α-TRIHYDROXYCYCLOPENTANETRIOL.

Evidence for the intermediacy of a 4β-hydroxymethyl-1α,2α,3α-trihydroxycyclopentanetriol (5 or 6) in the biosynthesis of the nucleoside antibiotic aristeromycin (1) has been obtained by administration of doubly-labeled forms of D-glucose to the fermentation broth of Streptomyces citricolor followed by trapping of the tetrol 5 using isotope dilution methods.