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

Base Information

• Chemical Name: 4-O-(3,6-diazido-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin
• CAS No.: 189454-74-8
• Molecular Formula: C₃₅H₃₄N₆O₁₂
• Molecular Weight: 730.688
• Mol file: 189454-74-8.mol

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

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

There total 10 articles about 4-O-(3,6-diazido-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: 94.0%

4-O-(3,6-diazido-2,3,6-trideoxy-4-O-azidoacetyl-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin (189454-72-6) → 4-O-(3,6-diazido-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin (189454-74-8)

Guidance literature:

With Amberlite resin IRA 410 (OH^-); In methanol; dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jm9800752

Reference yield:

4'-demethylepipodophyllotoxin (6559-91-7) → 4-O-(3,6-diazido-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin (189454-74-8)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 90 percent / NaN₃ / dimethylformamide / 64 h / Ambient temperature

4: 94 percent / Amberlite resin IRA 410 (OH^-) / CH₂Cl₂; methanol / 3 h / 20 °C

With sodium azide; Amberlite resin IRA 410 (OH^-); boron trifluoride diethyl etherate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9800752

Reference yield:

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9) → 4-O-(3,6-diazido-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin (189454-74-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / -15 - 0 °C

2: 90 percent / NaN₃ / dimethylformamide / 64 h / Ambient temperature

3: 94 percent / Amberlite resin IRA 410 (OH^-) / CH₂Cl₂; methanol / 3 h / 20 °C

With sodium azide; Amberlite resin IRA 410 (OH^-); boron trifluoride diethyl etherate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9800752

upstream raw materials:

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

4'-demethylepipodophyllotoxin

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

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