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

Base Information

• Chemical Name: methyl(benzyl 2-O-benzoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside
• CAS No.: 219595-95-6
• Molecular Formula: C₄₉H₄₆O₁₆
• Molecular Weight: 890.895

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

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

Chemical Property:

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

There total 8 articles about methyl(benzyl 2-O-benzoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-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:

methyl(benzyl 2-O-benzoyl-4-O-levulinyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside → methyl(benzyl 2-O-benzoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside (219595-95-6)

Guidance literature:

With hydrazine hydrate; acetic acid; In pyridine; at 0 ℃; for 1h;

DOI:10.1016/S0008-6215(99)00067-1

Reference yield:

methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside (57784-06-2,6344-46-3) → methyl(benzyl 2-O-benzoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside (219595-95-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / triflic acid; NIS; 4A molecular sieves / toluene / 2 h / -20 °C

2: AcOH; water / 4 h / 50 °C

3: triethylamine; DMAP / CH₂Cl₂ / 3 h / 50 °C

4: 38.5 g / triethylamine; DMAP / CH₂Cl₂

5: CrO₃; H₂SO₄ / acetone / 5 h / 0 °C

6: KHCO₃ / dimethylformamide / 20 °C

7: AcOH; hydrazine hydrate / pyridine / 1 h / 0 °C

With chromium(VI) oxide; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; water; potassium hydrogencarbonate; hydrazine hydrate; acetic acid; triethylamine; In pyridine; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Etherification / 2: Hydrolysis / 3: Etherification / 4: Acylation / 5: Oxidation / 6: Esterification / 7: deprotection;

DOI:10.1016/S0008-6215(99)00067-1

Reference yield:

ethyl 2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-1-thio-L-idopyranoside → methyl(benzyl 2-O-benzoyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside (219595-95-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / triflic acid; NIS; 4A molecular sieves / toluene / 2 h / -20 °C

2: AcOH; water / 4 h / 50 °C

3: triethylamine; DMAP / CH₂Cl₂ / 3 h / 50 °C

4: 38.5 g / triethylamine; DMAP / CH₂Cl₂

5: CrO₃; H₂SO₄ / acetone / 5 h / 0 °C

6: KHCO₃ / dimethylformamide / 20 °C

7: AcOH; hydrazine hydrate / pyridine / 1 h / 0 °C

With chromium(VI) oxide; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; water; potassium hydrogencarbonate; hydrazine hydrate; acetic acid; triethylamine; In pyridine; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Etherification / 2: Hydrolysis / 3: Etherification / 4: Acylation / 5: Oxidation / 6: Esterification / 7: deprotection;

DOI:10.1016/S0008-6215(99)00067-1

upstream raw materials:

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

methyl(2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside

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