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

Base Information

• Chemical Name: 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
• CAS No.: 181024-59-9
• Molecular Formula: C₅₄H₆₅N₃O₂₁
• Molecular Weight: 1092.12

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 11 articles about 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 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: 84.0%

methyl (methyl 2-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate (181024-57-7) + [6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-levulinyl-α-L-idopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate (181024-58-8) → 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)

Guidance literature:

With 4 A molecular sieve; t-butyldimethylsiyl triflate; In toluene; for 1.5h;

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

Reference yield:

methyl 3-O-benzyl-α-L-idopyranoside (181228-42-2) → 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)

Guidance literature:

Multi-step reaction with 9 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

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 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)

Guidance literature:

Multi-step reaction with 6 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

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 (methyl 2-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate

[6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-levulinyl-α-L-idopyranosyluronate)-β-D-glucopyranosyl] trichloroacetimidate

methyl 3-O-benzyl-α-L-idopyranoside

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

Downstream raw materials:

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

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