124648-31-3

Upstream product

• 124751-19-5 (2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol 
• 98-88-4 benzoyl chloride 
• 58871-09-3 6-O-tert-butyldimethylsilyl-D-glucal 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 
• 25878-60-8 D-galactose pentaacetate 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 4098-06-0 triacetyl-D-galactal 
• 21193-75-9 D-galactal 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 124581-41-5 Benzoic acid (2R,3R,4R)-3-(4-bromo-benzyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester 
• 617673-20-8 benzoic acid 3-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester 
• 114861-45-9 (-)-(2S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(benzoyloxy)-3,4-dihydro-2H-pyran 
• 114861-47-1 (-)-(2S,4S)-2-(hydroxymethyl)-4-(benzyloxy)-3,4-dihydro-2H-pyran 
• 114861-48-2 (-)-(2S,4S)-4-(benzyloxy)-3,4-dihydro-2H-pyran-2-carboxaldehyde 
• 114861-46-0 (-)-(2S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(benzyloxy)-3,4-dihydro-2H-pyran 
• 114861-57-3 Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylsulfanylthiocarboxyoxy-3,4-dihydro-2H-pyran-4-yl ester 
• 124581-53-9 (E)-(R)-1-[(2R,3aS,5R,6R,7aS)-6-(4-Bromo-benzyloxy)-2-methoxy-hexahydro-furo[3,2-b]pyran-5-yl]-pent-3-en-2-ol 
• 124581-53-9 (1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-3-<2(S)-hydroxy-3(E)-pentenyl>-8-(methyloxy)-2,7-dioxabicyclo<4.3.0>nonane 
• 124581-44-8 (3aR,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-bis-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one 
• 124581-45-9 (1S,3R,4S,5R,6R)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-5-(phenylseleno)-2,7-dioxabicyclo<4.3.0>nonan-8-one 
• 124581-43-7 N,N-dimethyl-(2S,5R,6R)-5-<(4'-bromobenzyl)oxy>-6-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-3,4-dideoxypyran-2-acetamide 
• 124581-46-0 (3aS,5R,6S,7R,7aR)-6-(4-Bromo-benzyloxy)-5-hydroxymethyl-7-phenylselanyl-hexahydro-furo[3,2-b]pyran-2-one 
• 124581-47-1 (1S,3R,4R,6S)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-2,7-dioxabicyclo<4.3.0>nonan-8-one 

Relevant academic research and scientific papers

Catalytic Activation of Cis-Vicinal Diols by Boronic Acids: Site-Selective Acylation of Carbohydrates

Site-selective acylation of unprotected carbohydrates by using stable, storable, and easily handled imidazole-containing organoboronic acid catalysts is described. This catalytic process with low catalyst loading enables the introduction of a wide variety of acyl functional groups into the equatorial position of cis-vicinal diols in unprotected hexapyranosides with excellent site selectivity. This is the first example that uses a Lewis base-containing boronic acid to enhance the nucleophilicity of hydroxy groups.

Synthesis of the JKLM-ring fragment of ciguatoxin

A stereoselective synthesis of the LM-ring fragment has been achieved starting from a sugar derivative. A stereoselective synthesis of the JKLM-ring fragment has been achieved through a coupling between two segments via heteroconjugate addition, seven-membered ether ring formation mediated by an acetylene cobalt complex, and spiroketalization reaction.

Synthesis of a Structurally Modified Glycal. (-)-(2R,4S)-2-Methyl-2-vinyl-4-(benzyloxy)-3,4-dihydro-2H-pyran

A synthetic procedure for the transformation of levoglucosan (4) to (-)-(2R,4S)-2-methyl-2-vinyl-4-(benzyloxy)-3,4-dihydro-2H-pyran (1) in 11 steps is described.The scheme relies on selective deoxygenation of the pair of α-hydroxyl groups, blocking of the β-hydroxyl, and formation of ester 16.The presence of the carboxylate group allows for stereocontrolled methylation of the enolate anion, conversion of ester to vinyl, and ultimate eliminative removal of the methoxyl substituent in methyl glycoside 25.This key transformation takes advantage of regioselective acetal cleavage by trimethylsilyl iodide and in situ dehydroiodination of the product so formed with hexamethyldisilazane.Certain unsuccessful attempts to form the α-lithio anion of 1 are also discussed.