53008-65-4

Basic information

• Product Name: Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside
• Synonyms: METHYL 2,3,4-TRI-O-BENZYL-ALFA-D-GLUCOPYRANOSIDE;METHYL 2,3,4-TRI-O-BENZYL-ALPHA-D-GLUCOPYRANOSIDE;Methyl 2,3,4-tris-O-(phenylmethyl)--a-D-glucopyranoside;Methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside;methyl 4-O-(S)-benzyl-α-d1-2,3-di-O-benzyl-α-D-glucopyranoside;((2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methanol;Methyl 2,3,4-Tri-O-benzyl-α-3,4,5-Tris(benzyloxy)
• CAS NO: 53008-65-4
• Molecular Formula: C₂₈H₃₂O₆
• Molecular Weight: 464.55
• Product Categories: Sugars;Biochemistry;Glucose;Glycosides;O-Substituted Sugars;Carbohydrates & Derivatives
• Mol File: 53008-65-4.mol
• Article Data: 162

Chemical Properties

• Melting Point: 67 °C
• Boiling Point: 593 °C at 760 mmHg
• Flash Point: 312.5 °C
• Appearance: /
• Density: 1.2 g/cm³
• Vapor Pressure: 6.55E-15mmHg at 25°C
• Refractive Index: 24.5 ° (C=1, CHCl3)
• Storage Temp.: Freezer
• PKA: 14.48±0.10(Predicted)
• BRN: 1442065
• CAS DataBase Reference: Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside(53008-65-4)
• EPA Substance Registry System: Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside(53008-65-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 53008-65-4(Hazardous Substances Data)

Usage

Description

Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside is a synthetic compound derived from alpha-D-glucopyranoside, a monosaccharide. It is characterized by the presence of three benzyl groups attached to the 2nd, 3rd, and 4th hydroxyl groups of the glucopyranoside ring. This modification enhances its reactivity and stability in various chemical reactions, making it a valuable intermediate in organic synthesis.

Uses

Used in Organic Synthesis:
Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside is used as a key intermediate in the synthesis of various complex organic molecules, particularly in the field of carbohydrate chemistry. Its benzyl-protected structure allows for selective functionalization and manipulation of the molecule, facilitating the construction of more intricate carbohydrate structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside is utilized as a building block for the development of novel drug candidates. Its unique structure and reactivity enable the creation of new molecules with potential therapeutic applications, such as antibiotics, antivirals, and anticancer agents.
Used in Material Science:
Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside also finds applications in material science, where it can be used to develop new polymers and materials with specific properties. Its ability to form complex structures and interact with other molecules makes it a promising candidate for the development of advanced materials with applications in various industries, such as electronics, automotive, and aerospace.
Used in Research and Development:
In academic and industrial research settings, Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside serves as an important compound for studying the fundamental aspects of carbohydrate chemistry and its role in biological systems. It is also used as a reference material for the development and optimization of new synthetic methods and techniques in organic chemistry.

InChI:InChI=1/C28H32O6/c1-30-28-27(33-20-23-15-9-4-10-16-23)26(32-19-22-13-7-3-8-14-22)25(24(17-29)34-28)31-18-21-11-5-2-6-12-21/h2-16,24-29H,17-20H2,1H3/t24-,25-,26+,27-,28+/m1/s1

Upstream product

• 100-44-7 benzyl chloride 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 13035-24-0 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 620-05-3 iodomethylbenzene 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 
• 616883-87-5 methyl 2,3,4-tri-O-benzyl-6-O-phthalimidomethyl-α-D-glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 1085377-61-2 methyl 2,3,4-tri-O-benzyl-6-(4'-(o-nitrophthalimido)butyryl)-α-D-glucopyranoside 
• 1079205-73-4 C₃₇H₅₂O₆Si 
• 18685-19-3 methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-galactopyranoside 
• 1206803-23-7 methyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-α-D-galactopyranoside 

Downstream Products

• 131919-44-3 C₆₂H₅₈O₁₅ 
• 75336-65-1 methyl 2,3,4-tri-O-benzyl-α-D-glucopyranuronate 
• 86883-48-9 methyl 6-O-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 86883-47-8 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-α-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 56632-57-6 methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside 
• 61474-61-1 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-α-D-glucopyranoside 
• 97321-72-7 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-phenylseleno-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 
• 90124-30-4 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 109681-25-6 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 121237-83-0 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-pent-4-enyloxymethoxymethyl-tetrahydro-pyran 
• 142025-31-8 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-octyloxymethyl-tetrahydro-pyran 
• 142025-32-9 (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-decyloxymethyl-6-methoxy-tetrahydro-pyran 

Relevant articles and documents

Photolabile 2-(2-Nitrophenyl)-propyloxycarbonyl (NPPOC) for Stereoselective Glycosylation and Its Application in Consecutive Assembly of Oligosaccharides

A photolabile protecting group (PPG) 2-(2-nitrophenyl)-propyloxycarbonyl (NPPOC) was explored in glycosylation and applied in the consecutive synthesis of oligosaccharides. NPPOC displays a strong neighboring group participation (NGP) effect to facilitate the construction of 1,2-trans glycosides in excellent yield. Notably, NPPOC could be efficiently removed by photolysis, and the deprotection conditions are friendly to typical protecting groups. A branched and asymmetric oligomannose Man6 was rapidly prepared, and the consecutive assembly of oligosaccharides without intermediate purification was further investigated owing to the compatibility conditions between NPPPOC's photolysis and glycosylation.

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides

A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is