methyl [methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate

Base Information

• Chemical Name: methyl [methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate
• CAS No.: 181024-60-2
• Molecular Formula: C₄₉H₅₉N₃O₁₉
• Molecular Weight: 994.016

Synonyms:methyl [methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate

Chemical Property of methyl [methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate

Chemical Property:

Purity/Quality:

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Technology Process of methyl [methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate

There total 12 articles about methyl [methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]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: 96.0%

methyl O-(methyl-2-O-acetyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl-uronate)-(1->4)-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-methyl-2-O-allyl-3-O-benzyl-α-L-idopyranosiduronate (181024-59-9) → methyl [methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate (181024-60-2)

Guidance literature:

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

DOI:10.1016/0957-4166(96)00412-0

Reference yield:

methyl 3-O-benzyl-α-L-idopyranoside (181228-42-2) → methyl [methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate (181024-60-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 86 percent / 10-D,L-camphorsulphonic acid / 4 h / Ambient temperature

2: 85 percent / NaH / dimethylformamide / 2 h

3: 93 percent / 80percent AcOH / 0.5 h / 80 °C

4: Et₃N, dimethylaminopyridine / CH₂Cl₂ / 2 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 8 h

6: CrO₃, aq. H₂SO₄ / acetone / 3 h

7: ethyl acetate; diethyl ether / 0.17 h

8: 83 percent / hydrazine hydrate, AcOH, pyridine / 1 h / 0 °C

9: 84 percent / TBDMSOTf, molecular sieves 4A / toluene / 1.5 h

10: 96 percent / hydrazine hydrate, AcOH, pyridine / 1 h / 0 °C

With pyridine; chromium(VI) oxide; dmap; 4 A molecular sieve; sulfuric acid; t-butyldimethylsiyl triflate; (1S)-10-camphorsulfonic acid; sodium hydride; hydrazine hydrate; acetic acid; triethylamine; In diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/0957-4166(96)00412-0

Reference yield:

methyl 2-O-allyl-3-O-benzyl-α-L-idopyranoside (181024-54-4) → methyl [methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate (181024-60-2)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N, dimethylaminopyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 8 h

3: CrO₃, aq. H₂SO₄ / acetone / 3 h

4: ethyl acetate; diethyl ether / 0.17 h

5: 83 percent / hydrazine hydrate, AcOH, pyridine / 1 h / 0 °C

6: 84 percent / TBDMSOTf, molecular sieves 4A / toluene / 1.5 h

7: 96 percent / hydrazine hydrate, AcOH, pyridine / 1 h / 0 °C

With pyridine; chromium(VI) oxide; dmap; 4 A molecular sieve; sulfuric acid; t-butyldimethylsiyl triflate; hydrazine hydrate; acetic acid; triethylamine; In diethyl ether; dichloromethane; ethyl acetate; acetone; toluene;

DOI:10.1016/0957-4166(96)00412-0

upstream raw materials:

methyl O-(methyl-2-O-acetyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl-uronate)-(1->4)-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-methyl-2-O-allyl-3-O-benzyl-α-L-idopyranosiduronate

methyl 3-O-benzyl-α-L-idopyranoside

methyl 2-O-allyl-3-O-benzyl-α-L-idopyranoside

methyl 2-O-allyl-3-O-benzyl-4,6-O-isopropylidene-α-L-idopyranoside

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