54522-57-5

Basic information

• Product Name: methyl-2,3-di-O-benzyl-6-O-(4-toluenesulfonyl)-α-D-glucopyranoside
• Synonyms: methyl-2,3-di-O-benzyl-6-O-(4-toluenesulfonyl)-α-D-glucopyranoside
• CAS NO: 54522-57-5
• Molecular Weight: 528.623
• Mol File: 54522-57-5.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: methyl-2,3-di-O-benzyl-6-O-(4-toluenesulfonyl)-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl-2,3-di-O-benzyl-6-O-(4-toluenesulfonyl)-α-D-glucopyranoside(54522-57-5)
• EPA Substance Registry System: methyl-2,3-di-O-benzyl-6-O-(4-toluenesulfonyl)-α-D-glucopyranoside(54522-57-5)

Safety Data

• Hazardous Substances Data: 54522-57-5(Hazardous Substances Data)

Upstream product

• 87326-89-4 methyl 4-O-acetyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 87326-90-7 methyl 4-O-acetyl-2,3-di-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranoside 
• 76491-08-2 methyl 2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-glucopyranoside 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 149933-23-3 Methyl 2,3-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 56750-58-4 methyl 6-deoxy-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside 
• 87326-88-3 methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside 
• 190435-68-8 methyl 2,3-di-O-benzyl-4,6-di-O-tosyl-α-D-glucopyranoside 
• 366801-70-9 methyl 2,3-di-O-benzyl-4-O-crotonyl-6-O-p-toluenesulfonyl-α-D-glucopyranoside 

Relevant articles and documents

Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study

A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism studies indicated that FeCl3 initially formed [Fe(btfa)3] (btfa = benzoyl trifluoroacetonate) with twice the amount of Hbtfa under basic conditions in the solvent acetonitrile at room temperature. Then, Fe(btfa)3 and two hydroxyl groups of the substrates formed a five- or six-membered ring intermediate in the presence of the base. The subsequent reaction between the cyclic intermediate and a sulfonylation reagent led to the selective sulfonylation of the substrate. All key intermediates were captured in the high-resolution mass spectrometry assay, therefore demonstrating this mechanism for the first time.

Application of the Synthetic Aminosugars for Glycodiversification: Synthesis and Antimicrobial Studies of Pyranmycin

A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

Total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide, a new biologically active δ-lactone produced by Seiridium unicorne

The first total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5- olide (1), a new biologically active δ-lactone produced by Seiridium unicome, was accomplished from (R)-malic acid. In connection with the determination of the absolute configuration of 1, (2R,3S,5R)-(+)-2,3- dihydroxytetradecan-5-olide (ent-1) was also synthesized from D-glucose.