162239-10-3

Basic information

• Product Name: 1-deoxy-1-β-ethenyl-2,3,5-tri-O-benzyl-L-xylose
• Synonyms: 1-deoxy-1-β-ethenyl-2,3,5-tri-O-benzyl-L-xylose
• CAS NO: 162239-10-3
• Molecular Weight: 430.544
• Mol File: 162239-10-3.mol

Chemical Properties

• CAS DataBase Reference: 1-deoxy-1-β-ethenyl-2,3,5-tri-O-benzyl-L-xylose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-deoxy-1-β-ethenyl-2,3,5-tri-O-benzyl-L-xylose(162239-10-3)
• EPA Substance Registry System: 1-deoxy-1-β-ethenyl-2,3,5-tri-O-benzyl-L-xylose(162239-10-3)

Safety Data

• Hazardous Substances Data: 162239-10-3(Hazardous Substances Data)

Upstream product

• 92619-92-6 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol 
• 180323-16-4 (2S,3R,4R,5S)-2,5-dihydroxy-1,3,4-tris(benzyloxy)-6-heptene 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 

Downstream Products

• 300807-66-3 Phosphoric acid (2R,3R,4R,5S)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylmethyl ester diphenyl ester 
• 300807-67-4 C₃₀H₃₀O₁₁P₂ 
• 300807-58-3 ((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol 
• 1053649-50-5 Phosphoric acid (2R,3S,4S,5S)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl ester diphenyl ester 
• 4429-47-4 D-Fructose-1,6-diphosphat 
• 287733-95-3 (2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 

Relevant articles and documents

Spontaneous cyclization of triflates derived from δ-benzyloxy alcohols: Efficient and general synthesis of C-vinyl furanosides

On reaction with triflic anhydride, the hept-1-enitols resulting from the Wittig reaction of tetra-O-benzyl D-hexopyranoses with [Ph3P=CH2] lead, in one step, to 3,6-anhydro-hept-1-enitol derivatives ('C-vinyl furanosides') in high y

A concise synthesis of 2,5-dideoxy-2,5-imino-d-mannitol (DMDP) and HomoDMDP from l-xylose

A short and practical procedure for the preparation of C-2 substituted polyhydroxypyrrolidines is described. The C-2 substituent is introduced by a stereoselective addition of a Grignard reagent to a 2,3,5-protected aldofuranose and the cyclization to the pyrrolidine ring system is performed through a bis-mesylation/double nucleophilic displacement sequence. The efficiency of the methodology was demonstrated by its application to the synthesis of HomoDMDP and DMDP.

An unexpected rearrangement during Mitsunobu epimerization reaction of sugar derivatives

Mitsunobu reaction on the glucose derivative (3S,4R,5R,6R)-3,4,5,7- tetrabenzyloxy-6-hydroxy-1-heptene yielded an unexpected rearrangement major product. Its structure was determined as (3R,4R,5R,6S)-4,5,6,7- tetrabenzyloxy-3-hydroxy-1-heptene. The suggested rearrangement mechanism involves an initial intramolecular cyclization, followed by ring opening by the nucleophile p-nitrobenzoate. Product distribution of the Mitsunobu reaction was substrate-dependent, with the corresponding mannose derivative (the 3R epimer) giving less of the initial intramolecular reaction products and the corresponding galactose derivative (the 5S epimer) yielding almost exclusively the expected epimerization product. Varying the Mitsunobu reaction conditions (addition of base and using nonpolar solvent) led to the expected epimerization product of the glucose derivative.

Synthesis of Selectively Labeled D-Fructose and D-Fructose Phosphate Analogues Locked in the Cyclic Furanose Form

2,5-Anhydroglucitol and 2,5-anhydromannitol and their 6-phosphate and 1,6-diphosphate derivatives are cyclic analogues of the α and β anomers of D-fructofuranose, D-fructofuranose-6-phosphate, and D-fructofuranose-1,6-diphosphate. They were synthesized from protected D-mannose or D-glucose. The synthetic method was developed with emphasis on selective 2H labeling of these compounds, as a model for 3H incorporation, which will be used for further biochemical studies. A key cyclization step, based on a benzyl ether nucleophilic attack on an activated alcohol, constructed the ring system. The stereochemistry at C2 (α/β anomers) and at C5 (D sugar) was controlled by selective epimerizations. Mono- and diphosphate analogues were obtained from the same intermediate by changing the sequence of deprotection and phosphorylation steps.