120693-82-5

Basic information

• Product Name: 3,5-Di-O-benzyl-α-D-xylofuranose
• Synonyms: 3,5-Di-O-benzyl-α-D-xylofuranose
• CAS NO: 120693-82-5
• Molecular Weight: 330.381
• Mol File: 120693-82-5.mol
• Article Data: 27

Chemical Properties

• CAS DataBase Reference: 3,5-Di-O-benzyl-α-D-xylofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Di-O-benzyl-α-D-xylofuranose(120693-82-5)
• EPA Substance Registry System: 3,5-Di-O-benzyl-α-D-xylofuranose(120693-82-5)

Safety Data

• Hazardous Substances Data: 120693-82-5(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 87-72-9 L-xylopyranose 
• 41546-31-0 L-xylose 
• 131156-47-3 (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane 
• 114861-22-2 1,2-O-isopropylidene-α-L-xylofuranose 
• 87-72-9 L-(-)-xylose 
• 120693-81-4 (3aS,5S,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)dimethyl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxole 
• 100-39-0 benzyl bromide 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 532-20-7 D-xylofuranose 
• 87-72-9 D-(+)-xylose 
• 22250-06-2 1,2-O-Cyclohexylidene-α-D-xylofuranose 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 79063-96-0 3,5-di-O-benzyl-1,2-O-cyclohexylidene-α-D-xylofuranose 

Downstream Products

• 79083-38-8 1-O-methyl 3,5-di-O-benzyl α(D)xylo-pentoaldofuranose 
• 118243-91-7 3,5-di-O-benzyl-1,2-O-sulfinyl-α-D-xylofuranose 
• 196867-42-2 1-((2R,3R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-3-iodo-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 185681-41-8 (E)-(1S,2R)-2-Benzyloxy-1-benzyloxymethyl-heptadec-3-enylamine 
• 185681-39-4 Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester 
• 185681-40-7 (2R,3R,4E)-1,3-Di-O-benzyl-2-O-methylsulfonyloctadec-4-ene-1,2,3-triol 
• 137410-26-5 (2S,3R,4E)-2-azido-1,3-dibenzyloxyoctadeca-4-ene 
• 148289-49-0 (2R,3R)-1,3-Di-O-benzyl-4-octadecene-1,2,3-triol 
• 148289-52-5 (2S,3R)-2-amino-1,3-(dibenzyloxy)-octadeca-4-ene 
• 148289-50-3 (2R,3R)-1,3-Di-O-benzyl-2-O-(methylsulfonyl)-4-octadecene-1,2,3-triol 
• 148289-53-6 (2S,3R)-1,3-di-O-benzyl-2-(N-tetradecanoylamino)-4-octadecene-1,3-diol 
• 134953-45-0 1-(3',5'-di-O-benzyl-β-D-xylo-furanosyl)thymine 
• 134953-44-9 (2'-O-acetyl-3',5'-di-O-benzyl-β-D-xylofuranosyl)-thymine 
• 146918-95-8 (2'-bromo-3',5'-di-O-benzyl-2'-deoxy-β-D-xylofuranosyl)thymine 

Relevant articles and documents

Conversion of D-xylose to protected D-lyxose derivatives and to D-lyxose, via the corresponding 1,2-anhydride

Acid hydrolysis of 3,5-di-O-benzyl-1,2-O-cyclohexylidene-α-D-xylofuranose gave the corresponding lactol, which was subsequently converted to the 3,5-di-O-benzyl-2-O-mesyl-D-xylofuranose. This compound readily reacted with sodium methoxide, sodium benzylate or sodium hydroxide (presumably via the corresponding 1,2-anhydride) to give the protected D-lyxofuranosides. These compounds were finally converted to methyl α-D-lyxopyranoside or to D-lyxose. Copyright (C) 1999 Elsevier Science Ltd.

Studies toward a synthesis of trilobatin B, a lignan from the liverwort Bazzania trilobata: Asymmetric construction of the tetrahydrofuran segment

A novel and stereocontrolled process is described for the asymmetric synthesis of the tetrahydrofuran segment of a 2,3-dicarboxy-6,7-dihydroxy-1- (3′,4′-dihydroxyphenyl)-1,2- dihydronaphthalene mono-ester, trilobatin B, a lignan from the liverwort Bazzani

PROCESSES FOR PREPARING 2-DIHALO RIBOLACTONES

Methods for forming 2-bromo, 2-fluoro ribofuranose intermediates and 2-chloro, 2- fluoro ribofuranose intermediates for use in preparing antiviral nucleosides are disclosed. Methods for forming nucleosides, and nucleoside prodrugs, using the intermediates, are also disclosed. The methods all produce intermediates, and the resulting nucleosides and prodrugs thereof, wherein the chirality of the carbon at the 2-position is controlled. In some embodiments, the chemistry involves using chiral auxiliaries, such as (R)-2,2-dimethyl-l,3- dioxolane-4-carbaldehyde, and in other embodiments, the chemistry involves using chiral starting materials, such as D-xylose.

Synthesis of purine nucleosides from D -glucuronic acid derivatives and evaluation of their cholinesterase-inhibitory activities

Glucuronolactones were used as precursors for N9 and N 7 purine nucleosides containing glucuronic acid derivatives in their structures. Acetylated N-benzylglucofuran- and glucopyranuronamides were synthesized in a few steps from glucofuranurono-6,3-lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide-based nucleosides by N-glycosylation with silylated 2-acetamido-6-chloropurine in the presence of trimethylsilyl triflate. The triacetylated bicyclic lactone was coupled itself with the nucleobase to give bicyclic N9,N7 nucleosides. Tri-O-acetylglucopyranurono-6,1-lactone was used for the first time as a glycosyl donor for N-glycosylation, and led to β-configured N9- and N7-linked purinylglucuronides under reaction conditions similar to those used with the 1-O-acetyl-substituted glycosyl donors. The cholinesterase inhibitory profiles of the synthetic nucleosides bearing glucuronic acid derivatives as glycons were evaluated, and they showed moderate selective acetylcholinesterase inhibitory activities (Ki = 14.78-50.53 μM). The best inhibition was shown by the furanosyl N 9-linked uronamide-based purine nucleoside. The synthesis of furanosyl and pyranosyl N9 and N7 purine nucleosides containing glucofuranurono-6,3-lactone, N-benzylglucuronamide, and glucuronic acid moieties is reported. Glucuronolactones were used as glycosyl donors or converted into suitable 1-O-acetyl derivatives for purine glycosylation. Some nucleosides showed moderate and selective inhibition of acetylcholinesterase. Copyright