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

• 79063-96-0 3,5-di-O-benzyl-1,2-O-cyclohexylidene-α-D-xylofuranose 
• 22250-06-2 1,2-O-Cyclohexylidene-α-D-xylofuranose 
• 87-72-9 L-xylopyranose 
• 100-44-7 benzyl chloride 
• 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 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 

Downstream Products

• 110237-88-2 1,4-anhydro-3,5-di-O-benzyl-2-deoxy-D-threo-pent-1-enitol 
• 521916-58-5 (3S,4S,5S)-4-Benzyloxy-5-benzyloxymethyl-2-(2,2,2-trichloro-ethoxy)-tetrahydro-furan-3-ol 
• 192565-69-8 1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfenyl-D-xylofuranose 
• 192565-68-7 {1-[1-((3R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-furan-3-yloxy)-meth-(Z)-ylidene]-2,2-dimethyl-propoxy}-tert-butyl-dimethyl-silane 
• 260403-56-3 1-deoxy-3,5-di-O-benzyl-2-O-(3,3-dimethyl-2-oxobutyl)-1-phenylsulfonyl-D-xylofuranose 
• 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 
• 146933-27-9 (2'R)(3',5'-di-O-benzyl-2'-deoxy-2'-deutero-β-D-xylofuranosyl)thymine 
• 146918-94-7 1-(3',5'-di-O-benzyl-2'-O-mesyl-β-D-xylo-furanosyl)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.

Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB

A diastereoselective concise synthesis of the iminosugars DMDP and DAB is presented starting from l-xylose and affording the two alkaloids in good yields of 35% and 22% over seven and eight steps, respectively. The Petasis borono-Mannich reaction of 3,5-di-O-benzyl-l-xylofuranose with benzylamine and (E)-styrylboronic acid served as the nitrogen-introducing key step furnishing the new C-N bond in an entirely diastereoselective manner. A chemo- and regioselective O-mesylation followed by an intramolecular SN2- cyclisation allowed the formation of the pyrrolidine ring. Ozonolysis of the styryl double bond and subsequent reduction to form the C-5 hydroxymethyl substituent followed by hydrogenolysis of the benzyl protecting groups concluded the DMDP synthesis. Furthermore, an unexpected fragmentation process during the ozonolysis reaction also gave access to the C-5 decarbinolated DMDP derivative DAB.