tert-butyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosid)uronate

Base Information

• Chemical Name: tert-butyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosid)uronate
• CAS No.: 151992-79-9
• Molecular Formula: C₃₃H₄₀O₈
• Molecular Weight: 564.676

Synonyms:tert-butyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosid)uronate

Chemical Property of tert-butyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosid)uronate

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Technology Process of tert-butyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosid)uronate

There total 2 articles about tert-butyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosid)uronate 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 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranoside (151992-78-8) + tert-butyl alcohol (75-65-0) → tert-butyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosid)uronate (151992-79-9)

Guidance literature:

With dipyridinium dichromate; acetic anhydride; In dichloromethane; for 6h; Ambient temperature;

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

Reference yield:

methyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside (152141-84-9) → tert-butyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosid)uronate (151992-79-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / Me₃SiCl, NaCNBH₃, molecular sieves / acetonitrile / 6 h / Ambient temperature

2: 75 percent / pyridinium dichromate, Ac₂O / CH₂Cl₂ / 6 h / Ambient temperature

With dipyridinium dichromate; chloro-trimethyl-silane; molecular sieve; acetic anhydride; sodium cyanoborohydride; In dichloromethane; acetonitrile;

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

Reference yield: 92.0%

tert-butyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosid)uronate (151992-79-9) → tert-Butyl (methyl 2,3-di-O-benzyl-β-D-glucopyranoside)uronate (151992-80-2)

Guidance literature:

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

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

upstream raw materials:

methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranoside

tert-butyl alcohol

methyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside

Downstream raw materials:

tert-Butyl (methyl 2,3-di-O-benzyl-β-D-glucopyranoside)uronate

Methyl O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-(1->4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(tert-butyl 2,3-di-O-benzyl-β-D-glucopyranosid)uronate

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