190952-23-9

Upstream product

• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 176848-45-6 (2R,3R,4R,5R)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexan-2-ol 
• 191211-54-8 (2R,3R,4R,5R)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-ol 
• 930113-63-6 2,3,4,6-tetra-O-benzyl-D-arabinohexos-5-ulose 
• 77638-00-7 2,3,4,6-tetra-O-benzyl-1,5-di-O-mesyl-D-glucitol 
• 77698-99-8 2,3,4,6-tetra-O-benzyl-1,5-di-O-mesyl-D-mannitol 
• 1376554-78-7 (2S,3S,4R,5S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)tetrahydro-2H-thiopyran 

Relevant academic research and scientific papers

Stereocontrolled formation of protected aminodeoxyalditols from simple carbohydrate precursors by debenzylating cycloetherification

A new and highly efficient methodology for the stereocontrolled synthesis of aminodeoxyalditols is described through a dimesylation/intramolecular SN2 nucleophilic substitution ringforming reaction sequence from glucose, mannose, and galactose derivatives

Diastereoselectivity of the cyclization of hexos-5-uloses by Sm2-mediated pinacol coupling

2,3,4,6-Tera-O-benzyl-hexos-5-uloses derived from D-glucose, D- mannose and D-galactose have been cyclized to cis-diols by a one pot Swerm oxidation/SmI2-mediated pinacol coupling procedure. The effect of the substituent orientation on the diastereoselectivity of the coupling step is examined.

An efficient activation of the hydroxyl function by (diethylamino)sulfur trifluoride (DAST): preparation of chiral polyoxygenated tetrahydrofurans by stereoselective benzyloxy group participation

Based on an intramolecular benzyloxy or amide group participation, two sets of experimental conditions have been established for the preparation of cis/trans tetrahydrofurans 6 or lactone 8 from sugar-derived open-chain hydroxylated precursors 4.These include: (1) a two-step mesylation-cyclization promoted by LiOH/THF-H2O or NaI/CH3CN at reflux; or (2) a one-step cyclization mediated by (diethylamino)sulfur trifluoride (DAST) at -78 deg C in CH2Cl2.The scope and limitations of these cyclizations are described particularly in relation to a stereoselective synthesis of highly oxygenated chiral tetrahydrofurans.Molecular modeling studies tentatively rationalized our experimental cyclization results affording five-membered versus six-membered heterocycles starting from different precursors. - Keywords: polyoxygenated tetrahydrofuran; (diethylamino)sulfur trifluoride (DAST); benzyl group participation; amide group participation; L-gulonolactone; differentially protected 1,4-diol

Total synthesis of deacetyl-caloporoside, a novel inhibitor of the GABA(A) receptor ion channel

The total synthesis of deacetyl-caloporoside (1) which contains a β-D-mannopyranoside unit has been accomplished by coupling of the disaccharide-like segment derived from methyl α-D-mannopyranoside, with the hydroxyheptadecyl salicylic acid segment. The biological activity of 1 has also been evaluated.