1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-6-iodo-L-glucopyranose

Base Information

• Chemical Name: 1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-6-iodo-L-glucopyranose
• CAS No.: 111275-49-1
• Molecular Formula: C₂₁H₂₆INO₉
• Molecular Weight: 563.343

Synonyms:1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-6-iodo-L-glucopyranose

Chemical Property of 1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-6-iodo-L-glucopyranose

Chemical Property:

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Technology Process of 1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-6-iodo-L-glucopyranose

There total 1 articles about 1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-6-iodo-L-glucopyranose 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:

acetic anhydride (108-24-7) + 2-N-(benzyloxycarbonyl)-2-deoxy-2-methylamino-L-glucopyranose → 1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-6-iodo-L-glucopyranose (111275-49-1)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; sodium iodide; Yield given. Multistep reaction; 1.) -40 deg C-0 deg C, 3h; 2.) DMF, 120 deg C, 2h;

DOI:10.1248/cpb.34.3741

Reference yield: 88.0%

1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-6-iodo-L-glucopyranose (111275-49-1) → 1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-L-glucopyranose (111275-50-4)

Guidance literature:

With hydrogen; nickel; In ethanol; for 3h;

DOI:10.1248/cpb.34.3741

Reference yield:

1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-6-iodo-L-glucopyranose (111275-49-1) → 3,4-di-O-acetyl-2'-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-L-glucopyranose

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / hydrogen / Raney Ni / ethanol / 3 h

2: hydrochloric acid, acetic acid

With hydrogenchloride; hydrogen; acetic acid; nickel; In ethanol;

DOI:10.1248/cpb.34.3741

upstream raw materials:

acetic anhydride

Downstream raw materials:

1,3,4-tri-O-acetyl-2-N-(benzyloxycarbonyl)-2,6-dideoxy-2-methylamino-L-glucopyranose

1-O-(2,6-dideoxy-2-amino-α-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin

1-O-(2,6-dideoxy-2-amino-β-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin

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