Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
• CAS No.: 128142-70-1
• Molecular Formula: C34H40O9Si
• Molecular Weight: 620.772
• Mol file: 128142-70-1.mol

Synonyms:Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside;Methyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-a-D-glucopyranoside

Chemical Property of Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

Chemical Property:

• PSA: 106.59000
• LogP: 6.05630

Purity/Quality:

97% ^*data from raw suppliers

Methyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

There total 5 articles about Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-benzoyl-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: 75.0%

methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside (63734-12-3,74247-81-7,74247-82-8,74264-88-3) + benzoyl chloride (98-88-4) → methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside (128142-70-1,853879-39-7)

Guidance literature:

In pyridine; at 0 - 20 ℃; for 18h;

DOI:10.1016/j.tet.2017.07.047

Reference yield:

methyl 2,3,4-tri-O-benzoylglucopyranoside (34234-44-1) + 2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4,6-O-benzylidene-D-mannopyranosyl-ortho-hexynylbenzoate → methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside + methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside + methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside (128142-70-1,853879-39-7)

Guidance literature:

methyl 2,3,4-tri-O-benzoylglucopyranoside; 2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4,6-O-benzylidene-D-mannopyranosyl-ortho-hexynylbenzoate; With (triphenylphosphine)gold(I) chloride; In chlorobenzene; at 0 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With silver tetrakis(pentafluorophenyl)borate; In diethyl ether; chlorobenzene; at 0 ℃; for 3h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/chem.201500648

Reference yield:

2-O-benzyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α/β-D-mannopyranoside → methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside + methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside + methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside (128142-70-1,853879-39-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 25 °C

2.1: (triphenylphosphine)gold(I) chloride / chlorobenzene / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

2.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere

With dmap; (triphenylphosphine)gold(I) chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; chlorobenzene;

DOI:10.1002/chem.201500648

upstream raw materials:

methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

benzoyl chloride

tert-butyldimethylsilyl chloride

methyl-alpha-D-glucopyranoside

Downstream raw materials:

methyl 2,3,4-tri-O-benzoylglucopyranoside

methyl 6-O-(2-O-benzoyl-3-O-para-methoxybenzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

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