methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside
• CAS No.: 151992-88-0
• Molecular Formula: C₄₇H₅₄O₁₄
• Molecular Weight: 842.937

Synonyms:methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside

Chemical Property of methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside

Chemical Property:

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Technology Process of methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside

There total 6 articles about methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside 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: 80.0%

methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside (151992-87-9) → methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside (151992-88-0)

Guidance literature:

With ammonium cerium(IV) nitrate; In dichloromethane; water; acetonitrile; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(93)84030-A

Reference yield:

benzoyl chloride (98-88-4) → methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside (151992-88-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / pyridine / CH₂Cl₂ / Ambient temperature

2: 70 percent / Me₃SiCl, NaCNBH₃, molecular sieves / acetonitrile / 6 h / Ambient temperature

3: 68 percent / pyridinium dichromate, Ac₂O / CH₂Cl₂ / 6 h / Ambient temperature

4: 1) DMTST, molecular sieves, 2) Et₃N / 1) CH₂Cl₂, r.t., 3 h, 2) 0 deg C, 30 min

5: 80 percent / ceric ammonium nitrate / CH₂Cl₂; acetonitrile; H₂O / 2 h / Ambient temperature

With pyridine; dipyridinium dichromate; chloro-trimethyl-silane; molecular sieve; ammonium cerium(IV) nitrate; acetic anhydride; sodium cyanoborohydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1016/0008-6215(93)84030-A

Reference yield:

ethyl 3-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside (151992-83-5) → methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside (151992-88-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / pyridine / CH₂Cl₂ / Ambient temperature

2: 70 percent / Me₃SiCl, NaCNBH₃, molecular sieves / acetonitrile / 6 h / Ambient temperature

3: 68 percent / pyridinium dichromate, Ac₂O / CH₂Cl₂ / 6 h / Ambient temperature

4: 1) DMTST, molecular sieves, 2) Et₃N / 1) CH₂Cl₂, r.t., 3 h, 2) 0 deg C, 30 min

5: 80 percent / ceric ammonium nitrate / CH₂Cl₂; acetonitrile; H₂O / 2 h / Ambient temperature

With pyridine; dipyridinium dichromate; chloro-trimethyl-silane; molecular sieve; ammonium cerium(IV) nitrate; acetic anhydride; sodium cyanoborohydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1016/0008-6215(93)84030-A

upstream raw materials:

methyl 4-O-acetyl-2,6-di-O-bennzyl-3-O-(tert-butyl 2-O-benzoyl-3-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside

benzoyl chloride

ethyl 3-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside

ethyl 2-O-benzoyl-3-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

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