4-O-(3-azido-2,3-dideoxy-4,6-di-O-chloroacetyl-α-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

Base Information

Chemical Name:4-O-(3-azido-2,3-dideoxy-4,6-di-O-chloroacetyl-α-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin
CAS No.:215935-14-1
Molecular Formula:C₃₉H₃₇Cl₂N₃O₁₅
Molecular Weight:858.64
Hs Code.:

Synonyms:4-O-(3-azido-2,3-dideoxy-4,6-di-O-chloroacetyl-α-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

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Chemical Property of 4-O-(3-azido-2,3-dideoxy-4,6-di-O-chloroacetyl-α-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

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Technology Process of 4-O-(3-azido-2,3-dideoxy-4,6-di-O-chloroacetyl-α-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

There total 5 articles about 4-O-(3-azido-2,3-dideoxy-4,6-di-O-chloroacetyl-α-D-arabino-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: 65.0%

: 23363-33-9
4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin

: 215935-11-8
tert-butyldimethylsilyl 3-azido-4,6-di-O-chloroacetyl-2,3-dideoxy-β-D-arabino-hexopyranoside

: 215935-14-1
4-O-(3-azido-2,3-dideoxy-4,6-di-O-chloroacetyl-α-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -35 ℃; for 48h;
DOI:10.1021/jm9800752

Reference yield:

: 6559-91-7
4'-demethylepipodophyllotoxin

: 215935-14-1
4-O-(3-azido-2,3-dideoxy-4,6-di-O-chloroacetyl-α-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

Guidance literature:: Multi-step reaction with 2 steps

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

2: 65 percent / TMSOTf, 4 Angstroem powdered molecular sieves / CH₂Cl₂ / 48 h / -35 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triethylamine; In dichloromethane;
DOI:10.1021/jm9800752

Reference yield:

: 4,6-di-O-acetyl-3-azido-2,3-dideoxy-D-erythro-hexopyranose

: 215935-14-1
4-O-(3-azido-2,3-dideoxy-4,6-di-O-chloroacetyl-α-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

Guidance literature:: Multi-step reaction with 4 steps

1: 43 percent / imidazole / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 18 h

2: 97 percent / sodium methoxide / methanol / 1.5 h / Ambient temperature

3: 92 percent / pyridine / CH₂Cl₂ / 4 h / -10 °C

4: 65 percent / TMSOTf, 4 Angstroem powdered molecular sieves / CH₂Cl₂ / 48 h / -35 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; In methanol; dichloromethane;
DOI:10.1021/jm9800752