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

Base Information

• Chemical Name: methyl (methyl 3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 1333164-14-9
• Molecular Formula: C₃₆H₄₄O₁₂
• Molecular Weight: 668.738

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

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

Chemical Property:

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

There total 5 articles about methyl (methyl 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: 95.0%

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) → methyl (methyl 3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (1333164-14-9)

Guidance literature:

With methanol; sodium methylate; for 2h;

DOI:10.1016/j.carres.2011.06.021

Reference yield: 46.0%

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) → methyl (methyl 3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (1333164-14-9) + methyl [methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate](1→4)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:

With potassium carbonate; In methanol; for 2h;

Reference yield:

C14H20O10 → methyl (methyl 3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (1333164-14-9)

Guidance literature:

Multi-step reaction with 4 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

4: methanol; sodium methylate / 2 h

With methanol; trimethylsilyl trifluoromethanesulfonate; sodium methylate; 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 (methyl 2,4-di-O-acetyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

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

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