162239-12-5

Upstream product

• 92619-92-6 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol 
• 4060-34-8 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride 
• 1826-67-1 vinyl magnesium bromide 
• 70613-79-5 2,3,5-tri-O-benzyl-D-arabinofuranosyl bromide 
• 79258-18-7 (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)hept-6-en-2-ol 
• 162239-11-4 (2S,3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-hept-6-en-2-ol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Downstream Products

• 300807-68-5 Phosphoric acid (2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylmethyl ester diphenyl ester 
• 41107-82-8 2,5-anhydro-D-mannitol 
• 52011-52-6 Phosphoric acid mono-((2R,3S,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl) ester 
• 102208-55-9 2,5-anhydro-3,4,6-tri-O-benzyl-D-mannitol 
• 94273-27-5 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose 
• 94283-95-1 (2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 

Relevant academic research and scientific papers

D-arbinose-based synthesis of homo-C-d4T and homo-C-thymidine

2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β and α-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. (Chemical Equation Presented).

Highly stereoselective synthesis of C-vinyl furanosides through acid-catalyzed SN2 inversion at the C-3 position of 1,2-dideoxy-hept-1-enitols

A highly stereoselective synthesis of C-vinyl furanosides through the SN2 inversion at the C-3 position of the 1,2-dideoxy-hept-1-enitols is disclosed. Treatment of the 1,2-dideoxy-hept-1-enitols with diphenylammonium trifluoromethanesulfonate as the acid catalyst produced the C-vinyl furanosides (3,6-anhydro-1,2-dideoxy-hept-1-enitol derivatives) via a subsequent SN2 intramolecular debenzyloxyation-cycloetherification reaction at the C-3 position.

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.

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