59433-13-5

Usage

Uses

Used in Organic Synthesis:
1,6-DI-O-ACETYL-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOPYRANOSE is used as a synthetic intermediate for the preparation of various complex organic molecules. Its unique structure allows for selective reactions and transformations, making it a versatile building block in the synthesis of pharmaceuticals, natural products, and other bioactive compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,6-DI-O-ACETYL-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOPYRANOSE is used as a key intermediate in the synthesis of glycoconjugates and glycoproteins. These biomolecules play crucial roles in various biological processes, including cell recognition, immune response, and cell signaling. 1,6-DI-O-ACETYL-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOPYRANOSE's ability to be selectively modified and functionalized makes it an essential component in the development of new drugs and therapeutic agents.
Used in Chemical Research:
1,6-DI-O-ACETYL-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOPYRANOSE is also utilized in chemical research for studying the reactivity and selectivity of various organic reactions. Its unique structure allows researchers to investigate the influence of protective groups on reaction outcomes and develop new synthetic methodologies for the preparation of complex molecules.

Upstream product

• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 84799-77-9 methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 173395-56-7 methyl 2,3,4,6-tetra-O-benzyl-1-thio-b-glucopyranoside 
• 20888-02-2 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-mannopyranose 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 
• 506-96-7 Acetyl bromide 
• 2466-76-4 N-Acetylimidazole 
• 71117-16-3 2,3,4-tri-O-benzyl-β-D-glucopyranose 

Downstream Products

• 121401-75-0 Acetic acid (1R,2R,3S,4S,5S)-2-((2S,3R,4S,5R,6R)-6-acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4-bis-benzyloxy-5-((1S,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-cyclohexylmethyl ester 
• 137063-19-5 7'-O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-2,3,4',5',6'-penta-O-benzyl-4,7-O-benzylidenevalidoxylamine A 
• 137063-19-5 7'-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2,3,4',5',6'-penta-O-benzyl-4,7-O-benzylidenevalidoxylamine A 
• 137063-30-0 4'-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-7'-O-benzoyl-2,3,5',6'-tetra-O-benzyl-4,7-O-benzylidenevalidoxylamine A 
• 137063-38-8 6''-O-acetyl-2,3,4,4',5',6',7',2'',3'',4''-deca-O-benzylvalidamycin D 
• 137063-28-6 7,2'',3'',4'',6'',6'''-hexa-O-acetyl-7'-O-benzoyl-2,3,5',6',2''',3''',4'''-hepta-O-benzylvalidamycin F 
• 119116-62-0 <(1R)-(1,3,5/2,4)-2,3,4-tribenzyloxy-5-benzyloxymethyl-1-cyclohexyl> 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 119116-62-0 <(1S)-(1,3,5/2,4)-2,3,4-tribenzyloxy-5-benzyloxymethyl-1-cyclohexyl> 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 119116-62-0 <(1R)-(1,2,4/3,5)-2,3,4-tribenzyloxy-5-benzyloxymethyl-1-cyclohexyl> 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 119116-62-0 <(1S)-(1,2,4/3,5)-2,3,4-tribenzyloxy-5-benzyloxymethyl-1-cyclohexyl> 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 124492-73-5 Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-3-((2S,3R,4S,5R,6R)-6-acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-6-((1R,2R,3S,4R,5R)-3,4-diacetoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 124492-69-9 Benzoic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-3-((2R,3R,4S,5R,6R)-6-acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-6-((1R,2R,3S,4R,5R)-3,4-diacetoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 88567-49-1 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose 
• 171243-42-8 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 

Relevant academic research and scientific papers

2-Diphenylphosphinonyl-acetyl as a Remote Directing Group for the Highly Stereoselective Synthesis of β-Glycosides

The configuration of the anomeric glycosidic linkages is crucial for maintaining the biological functions and activities of carbohydrate molecules. However, their stereochemistry control in glycosylation represents one of the most challenging tasks in car

Synthesis and biological evaluation of 1,6-bis-triazole-2,3,4-tri-O-benzyl-α-D-glucopyranosides as a novel α-glucosidase inhibitor in the treatment of Type 2 diabetes

A novel series of 1,6-bis-triazole-benzyl-α-glucoside derivatives (7a-7ee) were designed, synthesized and evaluated for inhibitory activity against α-glucosidase. Most of the synthesized compounds exhibited good activity with IC50 ranging from

Four Different Regioisomeric Polycarbonates Derived from One Natural Product, d -Glucose

Strategies for the preparation of polycarbonates, derived from the natural product d-glucose, which have the potential to degrade back into their bioresorbable starting material and CO2, were developed. By employing established carbohydrate pro

Method for preventing cancer metastasis

The present invention relates to the use of a specific family of glycerolipid compounds of formula (I) described in the detailed description or the manufacture of a medicament for the prevention or for the treatment of cancer metastasis.

Synthesis of potassium (2R)-2-O-α-d-glucopyranosyl-(1→6)-α-d-glucopyranosyl-2,3-dihydroxypropanoate a natural compatible solute

Ethyl 6-O-acetyl-2,3,4-tribenzyl-1-thio-d-glucopyranoside, as a mixture of anomers, was employed for the stereoselective synthesis of the potassium salt of (2R)-2-O-α-d-glucopyranosyl-(1→6)-α-d-glucopyranosyl-2,3-dihydroxypropanoic acid (α-d-glucosyl-(1→6

Indium(III) triflate: A highly efficient catalyst for reactions of sugars

Indium(III) trifluoromethanesulfonate has been found to be extremely efficient in catalyzing acyl transfer reactions of various carbohydrates and their derivatives. Selective acetolyses of certain benzyl ethers/isopropylidene acetals of sugars have been possible using In(OTf)3 in Ac2O (neat). Reaction of the per-O-acetate of 2-deoxy-2-phthalimido-D-glucose with benzyl mercaptan in the presence of In(OTf)3 led to the formation of the corresponding thioglycoside in high yield. Facile formation and hydrolysis of the isopropylidene and benzylidene acetals of various carbohydrates have also been achieved very efficiently in the presence of In(OTf)3. The results show great promise for In(OTf)3 in synthetic carbohydrate chemistry.

Synthesis of septanosides through an oxyglycal route

(Chemical Equation Presented) A new route to synthesize septanoside derivatives from protected 2-hydroxyglycals is reported. Ring expansion of a pyranoside to a septanoside was achieved through key reactions of a cyclopropanation, ring opening, oxidation,

Facile and regioselective preparation of partly O-benzylated d-glucopyranose acetates via acid-mediated simultaneous debenzylation-acetolysis

Fully O-benzylated methyl α-d-glucopyranoside shows a steady order in stepwise debenzylation when it is treated with sulfuric acid in acetic anhydride. Based on the order of debenzylation, regioselective preparations of 2,3,4-tri-, 2,3-, 2,4-, 3,4-di-, an

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.

A short access to the macrocyclic core of cycloviracin and glucolipsin

The macrocyclic core of cycloviracin and glucolipsin has been synthesised in ten steps from levoglucosan and (S)-(-)-dimethyl malate. The limited number of steps to obtain this macrolide makes it a valuable procedure for the synthesis of analogues of cycl