1-O-(2-N-(benzyloxycarbonyl)-2-deoxy-4:6-O-ethylidene-2-methylamino-β-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin

Base Information

• Chemical Name: 1-O-(2-N-(benzyloxycarbonyl)-2-deoxy-4:6-O-ethylidene-2-methylamino-β-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin
• CAS No.: 111275-69-5
• Molecular Formula: C₃₈H₄₁NO₁₄
• Molecular Weight: 735.742
• Mol file: 111275-69-5.mol

Synonyms:

Chemical Property of 1-O-(2-N-(benzyloxycarbonyl)-2-deoxy-4:6-O-ethylidene-2-methylamino-β-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-(2-N-(benzyloxycarbonyl)-2-deoxy-4:6-O-ethylidene-2-methylamino-β-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin

There total 14 articles about 1-O-(2-N-(benzyloxycarbonyl)-2-deoxy-4:6-O-ethylidene-2-methylamino-β-L-glucopyranosyl)-4'-O-demethyl-1-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:

2-deoxy-2-methylamino-L-glucopyranose hydrochloride (7474-39-7,18378-96-6,23846-26-6,33423-05-1,33423-23-3) → 1-O-(2-N-(benzyloxycarbonyl)-2-deoxy-4:6-O-ethylidene-2-methylamino-α-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin (111275-69-5,111322-28-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / sodium carbonate / H₂O; acetone / 1 h / 0 °C

2: 60 percent / conc. sulfuric acid / 3 h / Ambient temperature

3: 43 percent / 30percent sodium hydroxide / H₂O; dioxane / 0.5 h / Ambient temperature

4: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

5: 93 percent / H₂ / 10percent palladium on carbon / acetone / 2 h / -15 °C

6: boron trifluoride etherate / CH₂Cl₂ / 0.5 h / -18 °C

With pyridine; sodium hydroxide; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; sodium carbonate; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; water; acetone;

DOI:10.1248/cpb.34.3733

Reference yield:

2-deoxy-2-methylamino-L-glucopyranose hydrochloride (7474-39-7,18378-96-6,23846-26-6,33423-05-1,33423-23-3) → 1-O-(2-N-(benzyloxycarbonyl)-2-deoxy-4:6-O-ethylidene-2-methylamino-β-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin (111275-69-5,111322-28-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / sodium carbonate / H₂O; acetone / 1 h / 0 °C

2: 60 percent / conc. sulfuric acid / 3 h / Ambient temperature

3: 43 percent / 30percent sodium hydroxide / H₂O; dioxane / 0.5 h / Ambient temperature

4: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

5: 93 percent / H₂ / 10percent palladium on carbon / acetone / 2 h / -15 °C

6: boron trifluoride etherate / CH₂Cl₂ / 0.5 h / -18 °C

With pyridine; sodium hydroxide; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; sodium carbonate; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; water; acetone;

DOI:10.1248/cpb.34.3733

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 1-O-(2-N-(benzyloxycarbonyl)-2-deoxy-4:6-O-ethylidene-2-methylamino-α-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin (111275-69-5,111322-28-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / sodium carbonate / H₂O; acetone / 1 h / 0 °C

2: 60 percent / conc. sulfuric acid / 3 h / Ambient temperature

3: 43 percent / 30percent sodium hydroxide / H₂O; dioxane / 0.5 h / Ambient temperature

4: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

5: 93 percent / H₂ / 10percent palladium on carbon / acetone / 2 h / -15 °C

6: boron trifluoride etherate / CH₂Cl₂ / 0.5 h / -18 °C

With pyridine; sodium hydroxide; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; sodium carbonate; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; water; acetone;

DOI:10.1248/cpb.34.3733

upstream raw materials:

4'-O-chloroacetyl-4'-O-demethyl-1-epipodophyllotoxin

2-deoxy-2-methylamino-L-glucopyranose hydrochloride

benzyl chloroformate

benzyloxycarbonyl 2-N-(benzyloxycarbonyl)-2-deoxy-2-methylamino-4:6-ethylidene-L-glucopyranoside

Downstream raw materials:

1-O-(2-deoxy-4:6-O-ethylidene-2-methylamino-β-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin

1-O-(2-deoxy-4:6-O-ethylidene-2-methylamino-α-L-glucopyranosyl)-4'-O-demethyl-1-epipodophyllotoxin

Refernces