162239-07-8

Upstream product

• 79258-18-7 (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)hept-6-en-2-ol 
• 93125-77-0 (2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol 
• 62-23-7 4-nitro-benzoic acid 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 19493-09-5 Methylenetriphenylphosphorane 
• 180323-16-4 (2S,3R,4R,5S)-2,5-dihydroxy-1,3,4-tris(benzyloxy)-6-heptene 

Downstream Products

• 210286-15-0 (2S,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(S)-oxiranyl-tetrahydro-furan 
• 210286-14-9 (2S,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(R)-oxiranyl-tetrahydro-furan 
• 210286-23-0 (2S,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-((S)-1-methoxymethoxy-undec-3-ynyl)-tetrahydro-furan 
• 210286-17-2 (2S,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-((R)-1-methoxymethoxy-undec-3-ynyl)-tetrahydro-furan 
• 210286-22-9 (S)-1-((2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-undec-3-yn-1-ol 
• 210286-16-1 (R)-1-((2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-undec-3-yn-1-ol 
• 210286-19-4 (2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-3,4-diol 
• 287733-94-2 (2R,3S,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 

Relevant academic research and scientific papers

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.

Annonaceous acetogenins: Preparation of new methoxy substituted THF synthons from D-glucose

In connection with the synthesis of cytotoxic annonaceous acetogenin analogs, enantiomerically pure threo (and erythro)-trans THF synthons have been prepared from D-glucose. These synthons are characterized by the presence of two methoxy (or hydroxy) groups in the THF ring, each in a cis configuration with respect to the vicinal side chain.

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