4-O-(3-azido-6iodo-4-O-chloroacetyl-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

Base Information

• Chemical Name: 4-O-(3-azido-6iodo-4-O-chloroacetyl-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin
• CAS No.: 189454-66-8
• Molecular Formula: C₃₇H₃₅ClIN₃O₁₃
• Molecular Weight: 892.055
• Mol file: 189454-66-8.mol

Synonyms:4-O-(3-azido-6iodo-4-O-chloroacetyl-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

Chemical Property of 4-O-(3-azido-6iodo-4-O-chloroacetyl-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-(3-azido-6iodo-4-O-chloroacetyl-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

There total 7 articles about 4-O-(3-azido-6iodo-4-O-chloroacetyl-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin 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: 48.0%

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9) + tert-butyldimethylsilyl 3-azido-4-O-chloroacetyl-2,3,6-trideoxy-6-iodo-β-D-ribo-hexopyranoside (189454-64-6) → 4-O-(3-azido-6iodo-4-O-chloroacetyl-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin (189454-66-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -15 - 0 ℃; for 5h;

DOI:10.1021/jm9800752

Reference yield:

4'-demethylepipodophyllotoxin (6559-91-7) → 4-O-(3-azido-6iodo-4-O-chloroacetyl-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin (189454-66-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 48 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / -15 - 0 °C

With boron trifluoride diethyl etherate; triethylamine; In dichloromethane;

DOI:10.1021/jm9800752

Reference yield:

4,6-di-O-acetyl-3-azido-2,3-dideoxy-D-erythro-hexopyranose → 4-O-(3-azido-6iodo-4-O-chloroacetyl-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin (189454-66-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 20 percent / imidazole / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 18 h

2: 99 percent / sodium methoxide / methanol / 1.5 h / Ambient temperature

3: 65 percent / pyridine / 1.) 0 deg C, 1 h, 2.) RT, 18 h

4: 82 percent / sodium iodide / acetone / 72 h / Heating

5: 90 percent / pyridine / CH₂Cl₂ / 1 h / -10 °C

6: 48 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / -15 - 0 °C

With pyridine; 1H-imidazole; boron trifluoride diethyl etherate; sodium methylate; sodium iodide; In methanol; dichloromethane; acetone;

DOI:10.1021/jm9800752

upstream raw materials:

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin

tert-butyldimethylsilyl 3-azido-4-O-chloroacetyl-2,3,6-trideoxy-6-iodo-β-D-ribo-hexopyranoside

4'-demethylepipodophyllotoxin

tert-butyldimethylsilyl 3-azido-2,3,6-trideoxy-6-iodo-β-D-ribo-hexopyranoside

Downstream raw materials:

4-O-(3,6-diazido-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

4-O-(3,6-diazido-2,3,6-trideoxy-4-O-azidoacetyl-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

4-O-(3-azido-6-iodo-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin