2,3,4,6-Tetra-O-benzyl-D-glucopyranose - CAS 4132-28-9
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CAS 4132-28-9 2,3,4,6-Tetra-O-benzyl-D-glucopyranose

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1.Tuning of the prolyl trans/cis-amide rotamer population by use of C-glucosylproline hybrids.
Owens NW1, Braun C, Schweizer F. J Org Chem. 2007 Jun 22;72(13):4635-43. Epub 2007 May 31.
We describe the synthesis of a fused bicyclic C-glucosylproline hybrid (GlcProH) from commercially available 2,3,4,6-tetra-O-benzyl-d-glucopyranose. The GlcProH was incorporated into the model peptides Ac-GlcProH-NHMe and Ac-Gly-GlcProH-NHMe. Postsynthetic modifications can be introduced via derivatization of the carbohydrate scaffold. Conformational analysis of the GlcProH-modified model peptides shows that while the conformation of GlcProH remains fixed, the prolyl N-terminal amide equilibrium (Kt/c) can be varied with different modifications of the carbohydrate scaffold. Simple N-acyl derivatives studied by NMR spectroscopy showed that in CD3OD there was an increase in the cis-amide content as the sugar substituents changed from benzyl (10%) to hydroxyl (22%) to acetate (36%). Similar effects were observed in DMSO-d6. The exact nature of the influence is unclear, but it most likely arises through intramolecular interactions between sugar groups and the peptidic amide backbone.
2.Potential bile acid metabolites. 24. An efficient synthesis of carboxyl-linked glucosides and their chemical properties.
Lida T1, Nakamori R, Yabuta R, Yada S, Takagi Y, Mano N, Ikegawa S, Goto J, Nambara T. Lipids. 2002 Jan;37(1):101-10.
A facile and efficient synthesis of the carboxyl-linked glucosides of bile acids is described. Direct esterification of unprotected bile acids with 2,3,4,6-tetra-O-benzyl-D-glucopyranose in pyridine in the presence of 2-chloro-1,3,5-trinitrobenzene as a coupling agent afforded a mixture of the alpha- and beta-anomers (ca. 1:3) of the 1-O-acyl-D-glucoside benzyl ethers of bile acids, which was separated effectively on a C18 reversed-phase chromatography column (isolated yields of alpha- and beta-anomers are 4-9% and 12-19%, respectively). Subsequent hydrogenolysis of the alpha- and beta-acyl glucoside benzyl ethers on a 10% Pd-C catalyst in acetic acid/methanol/EtOAc (1:2:2, by vol) at 35 degrees C under atmospheric pressure gave the corresponding free esters in good yields (79-89%). Chemical specificities such as facile hydrolysis and transesterification of the acyl glucosides in various solvents were also discussed.
3.Neighboring group catalysis in the design of nucleotide prodrugs.
Khamnei S1, Torrence PF. J Med Chem. 1996 Sep 27;39(20):4109-15.
An approach is described for potential application to the delivery of polar nucleosides and nucleotides across lipophilic membranes, namely, nucleotide prodrugs based on salicyl phosphate. 3'-Azido-3'-deoxythymidine (AZT) and 3'-deoxythymidine (ddT) were chosen as models. For the synthesis of prototype compounds 1 and 2, the approach was first to react either methyl salicylate (for 1) or phenyl salicylate (for 2) with phosphorus oxychloride in dry methylene chloride at 0 degree C with the addition of triethylamine as acid scavenger. The resulting intermediate phosphorodichloridate was reacted immediately with excess nucleoside under the same conditions. The control model compound 3 was prepared by reaction of phenyl phosphorodichloridate and excess nucleoside in pyridine/methylene chloride at 0 degree C to give 3 in 82% yield. The synthesis of triester 7 involved reaction of alpha-(chloroacetyl)salicyl chloride with 2,3,4,6-tetra-O-benzyl-D-glucopyranose to give [[(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-oxy]carbonyl]-2- (1-chloroacetoxy)benzene (4) which was dechloroacetylated to 5,2,3,4,6-tetra-O-benzyl-D-glucopyranosyl salicylate.
4.Redox glycosidation: the use of Nozaki-Takai methylenylation in a highly stereoselective synthesis of sucrose.
Barrett AG1, Melcher LM, Bezuidenhoudt BC. Carbohydr Res. 1992 Aug 3;232(2):259-72.
Sequential reaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose (7) with butyllithium and 2-[2,3,5-tri-O-benzyl-4-O-(tert-butyldiphenylsilyl)-D- arabinonoyl]thio-3-nitropyridine (6) at -78 degrees gave 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl 2,3,5-tri-O-benzyl-4-O-(tert-butyldiphenylsilyl)-D-arabinonate+ ++ (8; 71%, alpha:beta greater than 50:1). Ester carbonyl methylenylation, desilylation, and iodoetherification in the presence of silica gave 3,4,6-tri-O-benzyl-1-deoxy-1-iodo-(2,3,4,6-tetra-O-benzyl-alpha-D- glucopyranosyl)-beta-D-fructofuranoside (15; 44%, alpha:beta greater than 50:1). This neopentylic iodide 15 was converted into sucrose (1;80%) by free-radical substitution using TEMPO (24) followed by sodium-ammonia reduction, acetylation, and Zemplén methanolysis.