O-benzyl-4,9-bis-epipodophyllotoxine

Base Information

• Chemical Name: O-benzyl-4,9-bis-epipodophyllotoxine
• CAS No.: 139253-55-7
• Molecular Formula: C₂₉H₂₈O₈
• Molecular Weight: 504.537
• Mol file: 139253-55-7.mol

Synonyms:O-benzyl-4,9-bis-epipodophyllotoxine

Chemical Property of O-benzyl-4,9-bis-epipodophyllotoxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-benzyl-4,9-bis-epipodophyllotoxine

There total 7 articles about O-benzyl-4,9-bis-epipodophyllotoxine 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: 71.0%

(3SR,4RS)-4-[(SR)-1,3-benzodioxol-5-yl(benzyloxy)-methyl]-3-[hydroxy(3,4,5-trimethoxyphenyl)methyl]dihydrofuran-2(3H)-one → 1,3,9β,9aα-tetrahydro-6,7,8-trimethoxy-9α-(3,4-methylenedioxyphenyl)naphtho<2,3-c>furan-3-one (118826-03-2,139219-21-9) + O-benzyl-4,9-bis-epipodophyllotoxine (139253-55-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tet.2006.01.038

Reference yield: 56.0%

2,3-trans-3-(α-benzyloxy-3,4-methylenedioxybenzyl)-2-(α-hydroxy-3,4,5-trimethoxybenzyl)butan-4-olide (139219-18-4,139343-41-2,139343-42-3,139343-43-4) → O-benzyl-4,9-bis-epipodophyllotoxine (139253-55-7) + 9-benzyloxy-4-(3,4-methylenedioxyphenyl)-5,6,7-trimethoxy-3a,4,9,9a-tetrahydronaphtho<2,3-c>furan-1(3H)-one (139219-20-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 0.5h; Ambient temperature;

Reference yield:

4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one (80483-34-7) → O-benzyl-4,9-bis-epipodophyllotoxine (139253-55-7)

Guidance literature:

Multi-step reaction with 5 steps

1: N-bromosuccinimide (NBS), peroxyde de benzoyle (POB) / CCl₄ / 1.75 h / Heating

2: 51 percent / H₂O / tetrahydrofuran / 48 h / Ambient temperature

3: 58 percent / KOH / dimethylsulfoxide / 0.67 h

4: 90 percent / hexamethyldisilylamidure de lithium (LHMDS) / benzene; hexane / 0.08 h / Ambient temperature

5: 7.4 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

With potassium hydroxide; N-Bromosuccinimide; Perbenzoic acid; boron trifluoride diethyl etherate; water; lithium hexamethyldisilazane; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; dimethyl sulfoxide; benzene;

upstream raw materials:

2,3-trans-3-(α-benzyloxy-3,4-methylenedioxybenzyl)-2-(α-hydroxy-3,4,5-trimethoxybenzyl)butan-4-olide

4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one

3,4,5-trimethoxy-benzaldehyde

3-(1-(hydroxy)-1-(3,4-methylenedioxyphenyl)methyl)-4-butanolide