25320-99-4

Basic information

• Product Name: BENZYL ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: BENZYL ALPHA-D-GLUCOPYRANOSIDE;1-O-Benzyl-α-D-glucopyranose;Benzyl α-D-Glucopyranoside (An alpha-beta mixture containing about 80% alpha)
• CAS NO: 25320-99-4
• Molecular Formula: C₁₃H₁₈O₆
• Molecular Weight: 270.28
• Mol File: 25320-99-4.mol
• Article Data: 38

Chemical Properties

• Melting Point: 122 °C
• Boiling Point: 480.178 °C at 760 mmHg
• Flash Point: 244.203 °C
• Appearance: /
• Density: 1.409 g/cm³
• PKA: 12.93±0.70(Predicted)
• CAS DataBase Reference: BENZYL ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL ALPHA-D-GLUCOPYRANOSIDE(25320-99-4)
• EPA Substance Registry System: BENZYL ALPHA-D-GLUCOPYRANOSIDE(25320-99-4)

Safety Data

• Hazardous Substances Data: 25320-99-4(Hazardous Substances Data)

Usage

General Description

Benzyl alpha-D-glucopyranoside is a chemical compound that belongs to the family of glucosides. It is derived from benzyl alcohol and alpha-D-glucose, and it is commonly used as a sugar substitute in food products. Benzyl alpha-D-glucopyranoside has also been reported to have potential pharmaceutical applications due to its anti-inflammatory and anti-tumor properties. Additionally, it is used in cosmetic and personal care products as a fragrance and flavoring agent. The chemical structure of benzyl alpha-D-glucopyranoside contains a benzene ring attached to a glucose molecule, making it a versatile compound with various industrial and commercial applications.

Upstream product

• 100-51-6 benzyl alcohol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 14897-51-9 Benzyl 3,4-O-isopropylidene-β-D-galactopyranoside 
• 1040165-33-0 benzyl 6-O-acetyl-β-D-galactopyranoside 
• 16741-14-3 benzyl 6-O-benzoyl-β-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 34246-23-6 benzyl D-glucopyranoside 
• 57-50-1 Sucrose 
• 34272-03-2 propargyl β-D-glucopyranoside 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 492-62-6 alpha-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 50-99-7 D-glucose 

Downstream Products

• 907573-18-6 benzyl-[O⁴,O⁶-((Ξ)-ethylidene)-β-D-galactopyranoside] 
• 56341-65-2 Benzyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 161955-13-1 benzyl 3,6-di-O-pivaloyl-β-D-galactopyranoside 
• 189878-82-8 C₃₃H₃₀O₁₀S₂ 
• 195316-78-0 benzyl 6-O-bromoacetyl-β-D-galactopyranoside 
• 78727-75-0 Benzyl 3,6-di-O-Allyl-β-D-galactopyranoside 
• 191546-23-3 benzyl 6-O-acetyl-α-D-glucopyranoside 
• 63879-95-8 benzyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside 
• 79549-73-8 benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside 
• 63283-86-3 benzyl 2-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranoside 
• 141410-44-8 benzyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside 
• 693219-39-5 benzyl 2-O-acetyl-β-D-galactopyranoside 
• 16741-15-4 benzyl 2-O-benzoyl-3-β-D-galactopyranoside 
• 693219-35-1 benzyl 6-O-(tert-butyldimethylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside 

Relevant articles and documents

Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions

A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.

Synthesis of the trisaccharide repeating unit of capsular polysaccharide from Klebsiella pneumoniae

The incidences of primary, pyrogenic liver abscess complicated by meningitis and septic endophthalmitis caused by Klebsiella pneumoniae has increased globally. Earlier studies have shown that the capsular polysaccharide (CPS) of Klebsiella pneumoniae plays an important role in the resistance to phagocytosis and related pathogenicity. The first chemical synthesis of the trisaccharide repeating unit of this CPS has been achieved via stereoselective glycosylation with orthogonal and appropriate protecting groups. A new method for the pyruvylation of trans diol was developed.

Multi-gram scale synthesis of a bleomycin (BLM) carbohydrate moiety: exploring the antitumor beneficial effect of BLM disaccharide attached to 10-hydroxycamptothecine (10-HCPT)

The “tumor-seeking” role of bleomycin (BLM) disaccharide has been demonstrated to serve as a promising tool for cancer diagnosis and a potential ligand for targeted therapy. However, these practical applications are often hampered by the lack of BLM disaccharide. Herein, an efficient multi-gram synthesis of peracetylated BLM disaccharide 20 is achieved by a TMSOTF-mediated glycosidation coupling manner in 43.6% overall yield in terms of benzyl galactoside. The critical innovation of the synthetic strategy is that inexpensive benzyl galactoside was first adopted to prepare an l-gulose subunit 3 as a glycosyl acceptor, with a much shorter route in 73.0% yield, and a 3-O-carbamoyl-mannose donor 4 was achieved in 47.2% yield by lowering the amount of dibutyltin oxide, and merging aminolysis and selective deacetylation into a one-pot reaction. Next, the incorporation of BLM disaccharide into 10-hydroxycamptothecin (10-HCPT), a non-specific model compound, to form conjugate 1 could significantly improve the antitumor activity and display obvious selectivity toward cancerous and normal cells in comparison with 10-HCPT. Moreover, BLM disaccharide itself was non-cytotoxic, clearly indicating the importance and potential of BLM disaccharide in solving the targeted antitumor therapy of cytotoxic drugs.