methyl (methyl 2,4-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl (methyl 2,4-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 1333164-13-8
• Molecular Formula: C₄₀H₄₈O₁₄
• Molecular Weight: 752.813

Synonyms:methyl (methyl 2,4-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl (methyl 2,4-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of methyl (methyl 2,4-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

There total 15 articles about methyl (methyl 2,4-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-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: 94.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + C14H18Cl3NO9 (1333164-12-7) → methyl (methyl 2,4-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (1333164-13-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 - 0 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2011.06.021

Reference yield: 90.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + C14H18Cl3NO9 → methyl (methyl 2,4-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (1333164-13-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;

Reference yield:

C14H20O10 → methyl (methyl 2,4-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (1333164-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1: benzylamine / tetrahydrofuran / 4 h

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -20 - 0 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; benzylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.carres.2011.06.021

upstream raw materials:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

C₁₄H₁₈Cl₃NO₉

methyl 4,6-O-benzylidene-α-D-glucopyranoside

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

methyl (methyl 3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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