61893-74-1

Usage

Derivative of α-D-galactopyranoside

a type of sugar molecule

Composed of

an allyl group and three benzyl groups attached to a galactopyranoside molecule

Potential applications

organic synthesis and as a building block for the production of other compounds

Valuable tool in

chemistry and pharmaceutical research.

Upstream product

• 59-23-4 D-Galactose 
• 112344-80-6 2-propenyl 2,3,4,6-tetra-O-benzyl-α-D-glactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-39-0 benzyl bromide 
• 37111-91-4 allyl 2,6-di-O-benzyl-α-D-galactopyranoside 
• 48149-72-0 (2S,3R,4S,5R,6R)-2-Allyloxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 107-18-6 allyl alcohol 
• 60478-61-7 allyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 
• 100759-11-3 allyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-α-D-galactopyranoside 
• 20746-64-9 allyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 100759-10-2 allyl 4,6-di-O-benzylidene-α-D-galactopyranoside 
• 2595-07-5 allyl D-galactopyranoside 
• 10257-28-0 D-Galactose 
• 100-44-7 benzyl chloride 

Downstream Products

• 167646-21-1 allyl 2,3,6-tri-O-benzyl-4-O-(trifluoromethylsulfonyl)-α-D-galactopyranoside 
• 24679-79-6 2,3,6-tri-O-benzyl-D-galactopyranose 
• 1079900-60-9 allyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-(1>4)-2,3,6-tri-O-benzyl-α-D-galactopyranoside 

Relevant academic research and scientific papers

5,5-Difluoro- and 5-Fluoro-5-methyl-hexose-based C-Glucosides as potent and orally bioavailable SGLT1 and SGLT2 dual inhibitors

(2S,3R,4R,5S,6R)-2-Aryl-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diols and (2S,3R,4R,5S,6R)-2-aryl-5-fluoro-5-methyl-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diols were discovered as dual inhibitors of sodium glucose co-transporter proteins (

5,5-DIFLUORO- AND 5-FLUORO-5-METHYL-C-GLYCOSIDE DERIVATIVES USEFUL AS DUAL SGLT1 / SGLT2 MODULATORS

The present invention is directed to 5,5-difluoro- and 5-fluoro-5-methyl-C-glycoside derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity.

BENZOCYCLOBUTANE DERIVATIVES USEFUL AS DUAL SGLT1/SGLT2 MODULATORS

The present invention is directed to benzocyclobutane derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

Synthesis of the Tetrasaccharide Repeating Unit from Acinetobacter baumannii Serogroup O18 Capitalizing on Phosphorus-Containing Leaving Groups

The first convergent synthesis of the tetrasaccharide repeating unit of the polymeric O antigen isolated from Acinetobacter baumannii serogroup O18 has been achieved. The ManNAcβ1→4Gal and GalNAcβ1→3Gal units were successfully obtained through β-selective

Tin-mediated regioselective benzylation and allylation of polyols: Applicability of a catalytic approach under solvent-free conditions

The first catalytic version of the stannylene-mediated benzylation and allylation of polyols is reported. The methodology is based on a simple solvent-free protocol that significantly advances, in terms of both experimental ease and synthetic scope, the a

An easy and versatile approach for the regioselective De-O-benzylation of protected sugars based on the I2/Et3SiH combined system

The use of cheap and easy to handle reagents, such as I2 and Et3SiH, at low temperature allows the regioselective removal of benzyl protecting groups from highly O-benzylated carbohydrates. The observed regioselectivity is dependent

Direct formation of β-glycosides of N-acetyl glycosamines mediated by rare earth metal triflates

A direct, mild and efficient protocol for the preparation of β-glycosides of N-acetyl glucosamine (GlcNAc) and N-acetyl galactosamine (GalNAc) has been developed using peracetylated β-GlcNAc and β-GalNAc as donors. All rare Earth metal triflate promoters

Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.

Syntheses of O-β-D-mannosyl-(1 → 4)-O-α-D-mannosyl-(1 → 3)-L-rhamnose and O-(2-acetamido-2-deoxy-β-D-mannosyl)-(1 → 4)-O-α-D-galactosyl-(1 → 4)-D-galactose via in-situ-activating glycosylation using 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucose

O-β-D-Mannopyranosyl-(1 → 4)-O-α-D-mannopyranosyl-(1 → 3)-L-rhamnopyranose, a trisaccharide including a repeating unit of the O-specific polysaccharide (OSP) of Bulkholderia vietnamiensis strain LMG 6988, and O-(2-acetamido-2-deoxy-β-D-mannopyranosyl)-(1 → 4)-O-α-D-galactopyranosyl-(1 → 4)-D-galactopyranose, a trisaccharide including a repeating unit of OSP of Acinetobactor baumannii serogroup O18, were synthesized by means of in-situ-activating glycosylation using 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose (2ATBG) and a reagent mixture of p-nitrobenzenesulfonyl chloride, silver triflate, and 1,8-diazabicyclo[5.4.0]undec-7-ene, and related systems. New syntheses of 2ATBG, allyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside, benzyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside, and 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-mannopyranose are described.

1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose as a glycosyl donor in syntheses of oligosaccharides

1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose was tested as a glycosyl donor for oligosaccharide synthesis via ferric chloride-catalyzed coupling reaction.Glycosyl acceptors tried (6 in all) were O-benzyl-protected D-galactosides having free OH groups at positions 3 and 4, respectively, and similarly protected glycosides of D-glucose and 2-acetamido-2-deoxy-D-glucose unsubstituted on O-4.Existing syntheses of all the acceptors were improved, in four instances by exploitation of Garegg and Hultberg's cyanoborohydride procedure for the conversion 4,6-O-benzylidene -> 6-O-benzyl .Good to excellent yields of β-linked disaccharides were obtained from the galactoside and glucoside acceptors, but with allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside, stereoselectivity was lost (α:β-ratio 1:2).Allyl and benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosides gave, respectively, the allyl and benzyl β-glycosides of the donor as major products.A mechanism is proposed for this transglycosidation reaction.The N-chloroacetyl groups in the disaccharide products were readily converted into N-acetyl by reduction with zinc-acetic acid.