113299-30-2

Basic information

• Product Name: 4a-carba-β-L-lyxofuranose
• CAS NO: 113299-30-2
• Molecular Weight: 148.159
• Mol File: 113299-30-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4a-carba-β-L-lyxofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 4a-carba-β-L-lyxofuranose(113299-30-2)
• EPA Substance Registry System: 4a-carba-β-L-lyxofuranose(113299-30-2)

Safety Data

• Hazardous Substances Data: 113299-30-2(Hazardous Substances Data)

Upstream product

• 1403598-64-0 (3aR,4R,5S,6aS)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 1403598-63-9 (3aS,6aS)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one 
• 1403598-61-7 (3aR,4R,6aS)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 112543-74-5 (1S,2S,4S)-4-(t-butyldiphenylsilyloxymethyl)-1,2-isopropylidenedioxy-3-cyclopentanone 
• 112574-58-0 (1S,2R,3S,4S)-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)cyclopentane 
• 112543-73-4 (1S,2S,3S,4S)-1-<((tert-butyldiphenylsilyl)-oxy)methyl>-2,3-(isopropylidenedioxy)cyclopenetane 
• 105285-29-8 (1S,2S,3S,4S)-2-acetoxy-1-(acetoxymethyl)-3,4-(isopropylidenedioxy)cyclopentane 
• 112543-75-6 (3aR,4S,5S,6aS)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 384341-73-5 (1S,4R,5R,6S)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-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 
• 384341-88-2 (S)-5-[(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-propyl]-dihydro-furan-2-one 
• 384341-71-3 (2S,2'S)-2-(tert-butyldimethylsilanyloxy)-(5-oxo-tetrahydrofuran-2-yl)acetaldehyde 
• 131530-77-3 (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])dihydrofuran-2-one 
• 127940-36-7 (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one 

Relevant articles and documents

Synthesis of 4a-carba-β-l-lyxofuranose, 4a-carba-β-l- arabinofuranose and 2,2,5-trimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one using Mn/CrCl3 mediated domino reactions and ring closing metathesis

A common method for the synthesis of 4a-carba-β-l-lyxofuranose and 4a-carba-β-l-arabinofuranose from d-mannose and 2,2,5-trimethyl-3a,6a- dihydro-cyclopenta[1,3]dioxol-4-one from d-ribose is described using catalytic Nozaki-Hiyama-Kishi (NHK) conditions and ring closing metathesis (RCM). In this transformation, ω-deoxy-ω-iodo manno/ribo furanoside undergoes reductive elimination in the presence of Mn/CrCl3 to give the corresponding olefin-aldehyde which was trapped by nucleophile under the same conditions to afford the desired diolefinic species. The ring closing metathesis reaction on these diolefinic species with Grubbs second generation catalyst produced the required carbocycles.

Synthesis of all stereoisomeric carbapentofuranoses

All carbocyclic analogs of the pentofuranoses were synthesized starting from norborn-5-en-2-one (1). By using either base- or acid-catalyzed Baeyer- Villiger reaction of 1, the central intermediates 2 and 3 were obtained. The required functionalization of the olefinic double bond was achieved either by cis-hydroxylation in the case of the ribo, lyxo, and α-xylo derivatives or by epoxidation and subsequent opening with aqueous perchloric acid. In the latter case, a pronounced selectivity for opening the epoxy alcohol in the 3- position was found. I an epoxy acetate with both functions on the same side of the ring was used, the eposide was opened in the 2-position by neighboring group participation of the acetate. The requisite side chain degradation was accomplished either by conversion of the ester into an olefin and subsequent dihydroxylation/cleavage reaction or by Curtius rearrangement to the amine and its conversion into an acetate.

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.