methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside
• CAS No.: 70774-92-4
• Molecular Formula: C₂₁H₂₄O₈S
• Molecular Weight: 436.483
• Mol file: 70774-92-4.mol

Synonyms:methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Methyl4-6-O-benzylidene-2-3-di-O-p-toluenesulfonyl-α-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside

There total 22 articles about methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

p-toluenesulfonyl chloride (98-59-9) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside (70774-92-4)

Guidance literature:

With sodium bromide; silver(l) oxide; In dichloromethane; at 20 ℃; for 24h; regioselective reaction;

DOI:10.1002/cctc.201601558

Reference yield: 66.0%

N-tosylimidazole (2232-08-8) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside (70774-92-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2004.05.129

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside (70774-92-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / TsOH / dimethylformamide / 45 °C

2: 66 percent / NaH / dimethylformamide

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2004.05.129

upstream raw materials:

methyl-[O³-benzoyl-O⁴,O⁶-((R)-benzylidene)-O²-(toluene-4-sulfonyl)-α-D-glucopyranoside]

2-methoxy-ethanol

sodium acetate

p-toluenesulfonylanhydride

Downstream raw materials:

methyl 3-azido-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside

methyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

methyl 2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Refernces

• 1、 Banerjee, Amit,Senthilkumar, Soundararasu,Baskaran, Sundarababu. "Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids". supporting information. p. 902 - 906. Retrieved 2016/01/16.
• 2、 Bauder, Claude. "A convenient synthesis of orthogonally protected 2-deoxystreptamine (2-DOS) as an aminocyclitol scaffold for the development of novel aminoglycoside antibiotic derivatives against bacterial resistance". supporting information; experimental part. p. 2952 - 2960. Retrieved 2009/02/02.