79083-32-2

Basic information

• Product Name: methyl 2,3,5-tri-O-benzyl-α-D-lyxofuranosiden
• Synonyms: methyl 2,3,5-tri-O-benzyl-α-D-lyxofuranosiden
• CAS NO: 79083-32-2
• Molecular Weight: 434.532
• Mol File: 79083-32-2.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: methyl 2,3,5-tri-O-benzyl-α-D-lyxofuranosiden(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,5-tri-O-benzyl-α-D-lyxofuranosiden(79083-32-2)
• EPA Substance Registry System: methyl 2,3,5-tri-O-benzyl-α-D-lyxofuranosiden(79083-32-2)

Safety Data

• Hazardous Substances Data: 79083-32-2(Hazardous Substances Data)

Upstream product

• 67737-48-8 methyl 5-benzyloxy-β-D-ribofuranoside 
• 100-44-7 benzyl chloride 
• 32780-15-7 methyl 5-O-benzyl-2,3-O-isopropylidene-α-D-lyxofuranoside 
• 63029-07-2 methyl 2,3-O-isopropylidene-α-D-lyxofuranoside 
• 100-39-0 benzyl bromide 
• 22416-73-5 methyl-α-D-lyxofuranoside 
• 79083-30-0 methyl 5-O-benzyl-α-D-lyxofuranoside 
• 1824-96-0 methyl ribofuranoside 
• 86883-41-2 2,3,5-tri-O-benzyl-α-D-ribofuranosyl fluoride 
• 33019-63-5 (2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran 
• 191543-71-2 methyl 3,5-di-O-benzyl-α-D-ribofuranoside 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 1825-61-2 Trimethylmethoxysilane 

Downstream Products

• 1428321-46-3 (1R,2R,3R,4R)-2,3,5-tris(benzyloxy)-1-methoxy-1-(phenylthio)pentan-4-ol 
• 1428321-63-4 (1R,2S,3S,4R)-2,3,5-tris(benzyloxy)-1-methoxy-1-(phenylthio)pentan-4-ol 
• 1428321-60-1 (1S,2S,3S,4R)-2,3,5-tris(benzyloxy)-1-methoxy-1-(phenylthio)pentan-4-ol 
• 93836-22-7 4,7-anhydro-5,6,8-tri-O-benzyl-1,2,3-trideoxy-D-altro-oct-1-enitol 
• 1330085-36-3 3-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-1-propyne 
• 1333119-56-4 C₃₆H₄₆O₅ 
• 1333119-55-3 4-penten-1-yl 2,3,5-tri-O-benzyl-α-D-lyxofuranoside 
• 1333119-43-9 C₃₆H₄₆O₅ 
• 1333119-42-8 4-penten-1-yl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 
• 1333119-54-2 C₅₄H₅₂O₁₃ 
• 79063-92-6 Acetic acid (1R,2S,3R)-3-acetoxy-2,4-bis-benzyloxy-1-(1-methoxy-ethyl)-butyl ester 
• 191543-71-2 methyl 3,5-di-O-benzyl-α-D-ribofuranoside 
• 92414-06-7 cyclohexyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 
• 92414-08-9 cyclohexyl 2,3,5-tri-O-benzyl-α-D-ribofuranoside 

Relevant articles and documents

Anodic coupling reactions and the synthesis of C-glycosides

A convenient, two-step procedure has been developed for converting sugar derivatives into C-glycosides containing a masked aldehyde functional group. The chemistry takes advantage of an anodic coupling reaction between an electron-rich olefin and an alcohol. The sequence works for the formation of both furanose and pyranose derivatives if less polarized vinyl sulfide derived radical cation intermediates are used. With more polarized enol ether derived radical cations, the cyclizations work best for the formation of furanose derivatives where the rate of five-membered ring formation precludes elimination reactions triggered by the radical cation.

Synthesis of β-D-ribofuranosyl-(1→3)-α-L-rhamnopyranose by in situ activating glycosylation using 1-OH sugar derivative and Me3SiBr-CoBr2-Bu4NBr-molecular sieves 4A system

Β-D-Ribofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)- L-rhamnopyranose, the trisaccharide repeating unit of the C. freundii O28, 1c O-specific polysaccharide, was synthesized using in situ activating glycosylation of the 1-OH sugar derivatives and a reagent mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and molecular sieves 4A. Regioselective tritylation was useful for synthesizing the 3-OH derivatives of methyl, allyl, and benzyl α-L-rhamnosides.

C-glycofuranosides via tandem Wittig-Michael sequence using a thiazole-armed phosphorane. A route to C-furanosyl α-hydroxy propanals and propionic acids

The reactions of 2-thiazolylcarbonylmethylenetriphenylphosphorane with five protected D-furanoses (manno, ribo, arabino, xylo, and lyxo) in refluxing toluene lead to mixtures of α- and β-1-C-(2-thiazolacyl)-glycosides (66-93 % overall yield). The β-linked C-glycosides derived from 2,3:5,6-di-O-isopropylidene-D-mannnofuranose was reduced to (R) and (S) akohols which after protection as O-benzyl ethers were transformed to α-alkoxy aldehydes by thiazole-to-formyl conversion; the aldehydes were oxidized to the corresponding α-alkoxy acids.