55628-54-1

Basic information

• Product Name: 3,4,6-Tri-O-benzyl-D-glucal
• Synonyms: 1,5-ANHYDRO-2-DEOXY-D-ARABINO-HEX-1-ENITOL 3,4,6-TRIBENZYL ETHER;1,5-ANHYDRO-2-DEOXY-D-LYXO-HEX-1-ENITOL 3,4,6-TRIBENZYL ETHER;1,5-ANHYDRO-3,4,6-TRI-O-BENZYL-2-DEOXY-D-ARABINOHEX-1-ENITOL;1,5-ANHYDRO-3,4,6-TRI-O-BENZYL-2-DEOXY-D-ARABINOHEX-1-ENE;TRI-O-BENZYL-D-ARABINOLACTONE;1,5-ANHYDRO-3,4,6-TRI-O-BENZYL-2-DEOXY-D- ARABINOHEX-1-ENITOL 99+%;(2R,3S,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran;Tri-O-benzyl-D-glucal 97%
• CAS NO: 55628-54-1
• Molecular Formula: C₂₇H₂₈O₄
• Molecular Weight: 416.51
• Product Categories: Biochemistry;Glucose;Glycals;Sugars;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis;Inhibitor;Polysaccharides
• Mol File: 55628-54-1.mol
• Article Data: 92

Chemical Properties

• Melting Point: 57-58 °C(lit.)
• Boiling Point: 494.82°C (rough estimate)
• Flash Point: 129.7 °C
• Appearance: White crystalline solid
• Density: 1.0800 (rough estimate)
• Vapor Pressure: 2.24E-11mmHg at 25°C
• Refractive Index: -2 ° (C=2.5, CH3CN)
• Storage Temp.: −20°C
• Water Solubility: Insoluble in water, easily soluble in CHCl3
• Sensitive: Hygroscopic
• BRN: 1691968
• CAS DataBase Reference: 3,4,6-Tri-O-benzyl-D-glucal(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-Tri-O-benzyl-D-glucal(55628-54-1)
• EPA Substance Registry System: 3,4,6-Tri-O-benzyl-D-glucal(55628-54-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 24/25-45-36/37/39-27-26
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 55628-54-1(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE POWDER

Uses

3,4,6-Tri-O-benzyl-D-glucal, is an important building block for both solid- and solution-phase synthesis of oligosaccharides.

InChI:InChI=1/C27H28O4/c1-4-10-22(11-5-1)18-28-21-26-27(31-20-24-14-8-3-9-15-24)25(16-17-29-26)30-19-23-12-6-2-7-13-23/h1-17,25-27H,18-21H2/t25-,26+,27-/m0/s1

Upstream product

• 52485-06-0 3,4,6-tri-O-acetyl-D-glucal 
• 111425-49-1 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 
• 2873-29-2 D-glucal triacetate 
• 2595-05-3 Diacetone D-glucose 
• 100-39-0 benzyl bromide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 111-71-7 heptanal 
• 168212-65-5 2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-sulfonyl)-pyridine 
• 168212-60-0 2-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-sulfonyl)-pyridine 
• 108-24-7 acetic anhydride 
• 165524-85-6 6-O-(benzyl)-D-glucal 
• 100-52-7 benzaldehyde 
• 96-22-0 pentan-3-one 

Downstream Products

• 132674-55-6 1-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-2,5-dione 
• 132674-54-5 1-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-2,5-dione 
• 120316-47-4 Acetic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester 
• 120316-50-9 Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester 
• 122194-14-3 (3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-phenylselanyl-tetrahydro-pyran-2-ol 
• 122194-14-3 2-deoxy-2-selenophenyl-3,4,6-tri-O-benzyl-α-glucopyranose 
• 128358-44-1 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-β-D-glucopyranosyl benzenesulfonamide 
• 128358-42-9 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-glucopyranosyl benzenesulfonamide 
• 128358-43-0 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranosyl benzenesulfonamide 
• 153289-67-9 1,1-dimethyl-2-propenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranoside 
• 139378-64-6 (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-(2,2-dimethyl-propoxy)-5-phenylsulfanyl-tetrahydro-pyran 
• 139378-63-5 (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-(2,2-dimethyl-propoxy)-5-phenylsulfanyl-tetrahydro-pyran 
• 81336-84-7 [2-((4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-trimethyl-silane 
• 141621-03-6 (2-deoxy-3,4,6-O-tribenzyl-α-D-glucopyranosyl)carboxaldehyde 

Relevant articles and documents

Synthesis of 2-iodoglycals, glycals, and 1,1′-disaccharides from 2-deoxy-2-iodopyranoses under dehydrative glycosylation conditions

(Chemical Equation Presented) Treatment of 2-deoxy-2-iodopyranoses under dehydrative glycosylation conditions afforded pyranose glycals, 2-iodoglycals, and 1,1′-disaccharides instead of the expected glycoside products. While the product distribution revea

Ir(I)-Catalyzed C?H Glycosylation for Synthesis of 2-Indolyl-C-Deoxyglycosides

The construction of 2-deoxy-C-glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2-indolyl-C-deoxyglycosides via Ir(I)-catalyzed, pyridine-group-directed C?H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β-configuration products. Gram-scale synthesis and several practical transformations were conducted for further applications. Meantime, we also explored the mechanism of this method and proposed a catalytic cycle. (Figure presented.).

Light-Mediated Cross-Coupling of Anomeric Trifluoroborates

Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report stereoselective C-arylation and etherification reactions of anomeric trifluoroborates derived from BMIDA esters. These react