5349-10-0

Usage

Chemical compound

A complex chemical compound used in organic synthesis and carbohydrate chemistry.

Derivative of mannose

A derivative of mannose, a naturally occurring sugar.

Glycosidic linkages

Commonly employed in the production of glycosidic linkages.

Benzylidene group

Has a benzylidene group attached to the mannose ring, which imparts unique properties and reactivity to the molecule.

Building block

Often used as a building block in the synthesis of natural products, pharmaceuticals, and other biologically active compounds.

Versatile reagent

The chemical structure makes it a versatile and valuable reagent in the field of organic chemistry.

InChI:InChI=1/C13H14O5/c14-9-8-6-15-13(16-8)11-10(9)17-12(18-11)7-4-2-1-3-5-7/h1-5,8-14H,6H2

Upstream product

• 530-26-7 D-Mannose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 14168-65-1 mannosan 

Downstream Products

• 71019-71-1 1,6-anhydro-2-O-benzoyl-3-bromo-3-desoxy-β-D-altopyranose 
• 162710-64-7 O-(2,3,4,6-Tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2,3-O-endo/exo-benzylidene-β-D-mannopyranose 
• 162710-65-8 O-(β-D-Galactopyranosyl)-(1->4)-1,6-anhydro-2,3-O-endo/exo-benzylidene-β-D-mannopyranose 
• 162710-66-9 O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2,3-O-endo/exo-benzylidene-β-D-mannopyranose 
• 162710-68-1 O-(3-O-Allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-β-D-mannopyranose 
• 162710-56-7 O-(3-O-Allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 162710-67-0 (1R,2S,6S,7R,8R)-7-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-phenyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane 
• 1054657-43-0 Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester 
• 162710-70-5 O-(2,3,4-Tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4)>-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 162710-69-2 O-(2,3,4-Tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4)>-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 90662-40-1 4-O-allyl-1,6-anhydro-3-O-benzyl-β-mannopyranose 
• 90662-41-2 4-O-allyl-2-O-(6-O-acetyl-2-O-allyl-3,4-di-O-benzoyl-α-D-galactopyranosyl)-1,6-anhydro-3-O-benzyl-β-mannopyranose 
• 90662-43-4 6-O-acetyl-4-O-allyl-2-O-(6-O-acetyl-2-O-allyl-3,4-di-O-benzoyl-α-D-galactopyranosyl)-3-O-benzyl-α-D-mannopyranosyl bromide 
• 90662-42-3 1,6-di-O-acetyl-4-O-allyl-2-O-(6-O-acetyl-2-O-allyl-3,4-di-O-benzoyl-α-D-galactopyranosyl)-3-O-benzyl-α-D-mannopyranose 

Relevant academic research and scientific papers

REACTION OF BUTYLLITHIUM WITH BENZYLIDENE ACETALS OF ALDOPYRANOSIDES AND 1,5-ANHYDROALDITOLS

Under suitable conditions, butyllithium selectively cleaves 5-membered benzylidene acetals (1,3-dioxolane ring) leaving the 6-membered analogs (1,3-dioxane ring) intact in aldopyranoside and 1,5-anhydroalditol derivatives.The usual course of the reaction

OUVERTURE PAR LE N-BROMOSUCCINIMIDE DES ACETALS BENZYLIDENIQUES DE METHYL-HEXOSIDES DE CONFIGURATION MANNO ET SYNTHESE DE LA N-ACETYL-L-MYCOSAMINE

Methyl 2,3:5,6-di-O-benzylidene-α-D-mannofuranoside and methyl 2,3-O-benzylidene-α-L-rhamnofuranoside were prepared according to a new procedure by simultaneous glycosidation and acetalation of D-mannose and L-rhamnose.Treatment of these compounds and of 1,6-anhydro-2,3-O-benzylidene-D-mannose with N-bromosuccinimide gave exclusively the 3-bromo compounds by regiospecific opening of the acetal ring.Thus, starting from rhamnose, N-acetyl-L-mycosamine (3-amino-3,6-dideoxy-L-mannose) was prepared in seven steps with a 32percent overall yield.