64768-20-3

Basic information

• Product Name: 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE
• Synonyms: 2,3,4,6-TETRA-O-BENZOYL-D-GLUCOPYRANOSE;2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSIDE;2,3,4,6-Tetra-O-benzoyl-beta-D-glucopyranose (YTT);2,3,4,6-Tetra-O-benzoyl-beta-D-glucopyranose;2,3,4,6-Tetra-O-benzoyl-D-glucopyranose
• CAS NO: 64768-20-3
• Molecular Formula: C₃₄H₂₈O₁₀
• Molecular Weight: 596.59
• Product Categories: Biochemistry;Glucose;O-Substituted Sugars;Sugars
• Mol File: 64768-20-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 151-156 °C
• Boiling Point: 744.233 °C at 760 mmHg
• Flash Point: 237.752 °C
• Appearance: /
• Density: 1.389 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: −20°C
• PKA: 11.20±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE(64768-20-3)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE(64768-20-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 64768-20-3(Hazardous Substances Data)

Usage

Description

2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE is a chiral building block that plays a crucial role in the synthetic preparation of saponins and glycosides. It is characterized by the presence of benzyl groups at the 2, 3, 4, and 6 positions, which contribute to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE is used as a chiral building block for the synthesis of saponins and glycosides, which are important compounds in the development of pharmaceuticals. These compounds have various biological activities, such as anti-inflammatory, antifungal, and antiviral properties, making them valuable for the treatment of various diseases and conditions.
Used in Organic Synthesis:
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE is also used as a versatile intermediate in organic synthesis. Its unique structure allows for various chemical reactions, such as glycosylation, to be performed, enabling the synthesis of a wide range of complex organic molecules with potential applications in various fields, including medicine, agriculture, and materials science.
Used in Research and Development:
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE serves as a valuable tool in research and development, particularly in the field of carbohydrate chemistry. Its unique properties and reactivity make it an ideal candidate for studying the structure, function, and interactions of carbohydrates, which can lead to a better understanding of their role in biological systems and the development of new therapeutic agents.

InChI:InChI=1/C34H28O10/c35-30(22-13-5-1-6-14-22)40-21-26-27(42-31(36)23-15-7-2-8-16-23)28(43-32(37)24-17-9-3-10-18-24)29(34(39)41-26)44-33(38)25-19-11-4-12-20-25/h1-20,26-29,34,39H,21H2/t26-,27-,28+,29-,34u/m1/s1

Upstream product

• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside 
• 105376-04-3 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 22415-91-4 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose 
• 492-62-6 alpha-D-glucopyranose 
• 7464-56-4 1-O-allyl-α-D-glucopyranoside 
• 1435780-53-2 allyl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 97590-76-6 benzyl-O-β-D-glucopyranoside 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-44-7 benzyl chloride 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose 
• 492-61-5 β-D-glucose 
• 41308-76-3 allyl α-D-mannopyranoside 

Downstream Products

• 278800-64-9 dihydrocholesteryl-2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 1218904-60-9 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-N,N,N',N'-tetraisopropylphosphorodiamidite 
• 865470-38-8 3-butenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 125367-09-1 n-pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 149707-76-6 O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) trichloroacetimidate 
• 149707-75-5 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 
• 1477511-05-9 C₄₅H₄₀NO₁₁P 
• 131150-08-8 benzyl β-D-galactopyranoside 2-(α-D-mannopyranosyl phosphate), ammonium salt 
• 131166-78-4 benzyl 3,4,6-tri-O-benzoyl-β-D-galactopyranoside 2-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl phosphate), triethylammonium salt 
• 131150-19-1 methyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside 4-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl phosphate), triethylammonium salt 
• 113567-42-3 5'-O-<<<<(2'',3'',4'',6''-tetra-O-benzoyl-α-D-mannopyranosyl)oxy>carbonyl>amino>sulfonyl>uridine 
• 183901-63-5 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 
• 118579-76-3 methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 128503-39-9 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-α-D-glucopyranoside 

Relevant articles and documents

Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides

The allylic bromination of allyl glycosides is conducted using NBS/AIBN reagents in (EtO)2CO and PhCF3 solutions, without using CCl4 as a solvent. The activated mixed halo-allyl glycosides led to glycosylations, mediated by a triflate, in a latent-active

Lewis acid promoted anomerisation of alkyl O- and S-xylo-, arabino- and fucopyranosides

Pentopyranoside and 6-deoxyhexopyranosides, such as those from D-xylose, L-arabinose and L-fucose are components of natural products, oligosaccharides or polysaccharides. Lewis acid promoted anomerisation of some of their alkyl O- and S-glycopyranosides i

Synthesis of a 1,3 β-glucan hexasaccharide designed to target vaccines to the dendritic cell receptor, Dectin-1

Transformation of 3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-d-glucofuranose into 2,4,6-tri-O-benzoyl-3-O-benzyl glucopyranosyl imidate proceeded efficiently via crystalline benzyl and per-benzoylated derivatives. This imidate glycosylated di-O-isopropylidene-α-d-glucofuranose in high yield and glycosylation of the disaccharide after removal of the 3′-O-benzyl ether afforded the β1,3 linked trisaccharide in excellent yield. Di- and trisaccharides imidates were readily prepared from the furanose terminated glycosylation products but both were unreactive in glycosylation reaction with the debenzylated di- and trisaccharide alcohols. The 3′-O-benzyl perbenzoylated disaccharide pyranose derivative could be selectively debenzoylated and converted to the corresponding perbenzoylated 4,6:4′,6′-di-O-benzylidene derivative. Lewis acid catalyzed glycosidation gave the selectively protected disaccharide ethylthioglycoside in good overall yield. Glycosidation of this thioglycoside donor with 5-methoxycarbonylpentanol gave the disaccharide tether glycoside and after catalytic removal of benzyl ether the resulting disaccharide alcohol was glycosylated by the thioglycoside in a 2+2 reaction to yield a tetrasaccharide. Repetition of selective deprotection of the terminal 3-O-benzyl ether followed by glycosylation by the disaccharide thioglycoside gave a protected hexasaccharide. Hydrogenolysis of this hexasaccharide followed by transesterification and second hydrogenolysis to remove a residual benzyl group gave the target hexasaccharide glycoside 1 as a Dectin-1 ligand functionalized to permit covalent attachment to glycoconjugate vaccines and thereby facilitate improved antigen processing by dendritic cells.