11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-(formylmethyl)-4-desoxypodophyllotoxin

Base Information

• Chemical Name: 11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-(formylmethyl)-4-desoxypodophyllotoxin
• CAS No.: 845863-43-6
• Molecular Formula: C₃₁H₂₈O₁₀
• Molecular Weight: 560.557
• Mol file: 845863-43-6.mol

Synonyms:11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-(formylmethyl)-4-desoxypodophyllotoxin

Chemical Property of 11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-(formylmethyl)-4-desoxypodophyllotoxin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-(formylmethyl)-4-desoxypodophyllotoxin

There total 7 articles about 11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-(formylmethyl)-4-desoxypodophyllotoxin 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:

Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-(2,3-dihydroxy-propyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester (845863-42-5) → 11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-(formylmethyl)-4-desoxypodophyllotoxin (845863-43-6)

Guidance literature:

With lead(IV) acetate; In benzene; at 20 ℃; for 3h;

DOI:10.1021/jm0495733

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-(formylmethyl)-4-desoxypodophyllotoxin (845863-43-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Et₃N / CH₂Cl₂

2: BF₃*Et₂O / CH₂Cl₂ / 4 h / 0 °C

3: N-methylmorpholine N-oxide; OsO₄ / acetone; 2-methyl-propan-2-ol / 3 h / 20 °C

4: Pb(OAc)4 / benzene / 3 h / 20 °C

With lead(IV) acetate; osmium(VIII) oxide; boron trifluoride diethyl etherate; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jm0495733

Reference yield:

4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol (153230-77-4) → 11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-(formylmethyl)-4-desoxypodophyllotoxin (845863-43-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves / CH₂Cl₂ / 2 h

1.2: tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h

2.1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 23 h

3.1: 82 percent / Et₃N / CH₂Cl₂

4.1: BF₃*Et₂O / CH₂Cl₂ / 4 h / 0 °C

5.1: N-methylmorpholine N-oxide; OsO₄ / acetone; 2-methyl-propan-2-ol / 3 h / 20 °C

6.1: Pb(OAc)4 / benzene / 3 h / 20 °C

With lead(IV) acetate; osmium(VIII) oxide; molecular sieve; tetrapropylammonium perruthennate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jm0495733

upstream raw materials:

Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-(2,3-dihydroxy-propyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester

benzyl chloroformate

4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol

11-oxo-13-deoxo-4'-demethylepipodophyllotoxin