13,20-epoxy-16β-ethoxy-3β-methoxy-21-nitrilo-12β-(phenylseleno)-picrasane

Base Information

• Chemical Name: 13,20-epoxy-16β-ethoxy-3β-methoxy-21-nitrilo-12β-(phenylseleno)-picrasane
• CAS No.: 105431-29-6
• Molecular Formula: C₂₉H₃₉NO₄Se
• Molecular Weight: 544.593

Synonyms:13,20-epoxy-16β-ethoxy-3β-methoxy-21-nitrilo-12β-(phenylseleno)-picrasane

Chemical Property of 13,20-epoxy-16β-ethoxy-3β-methoxy-21-nitrilo-12β-(phenylseleno)-picrasane

Chemical Property:

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Technology Process of 13,20-epoxy-16β-ethoxy-3β-methoxy-21-nitrilo-12β-(phenylseleno)-picrasane

There total 7 articles about 13,20-epoxy-16β-ethoxy-3β-methoxy-21-nitrilo-12β-(phenylseleno)-picrasane 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: 70.0%

potassium cyanide (151-50-8) + Methanesulfonic acid (2R,3aS,5R,6aS,7aR,8R,9R,11aR,11bS,11cS)-5-ethoxy-9-methoxy-8,11a-dimethyl-3-oxo-2-phenylselanyl-tetradecahydro-6-oxa-benzo[de]anthracen-11c-ylmethyl ester (105431-24-1) → 13,20-epoxy-16β-ethoxy-3β-methoxy-21-nitrilo-12β-(phenylseleno)-picrasane (105431-29-6)

Guidance literature:

With 18-crown-6 ether; In acetonitrile; for 16h; Ambient temperature;

DOI:10.1021/ja00238a022

Reference yield:

Phenylselenyl chloride (5707-04-0) → 13,20-epoxy-16β-ethoxy-3β-methoxy-21-nitrilo-12β-(phenylseleno)-picrasane (105431-29-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / tetrahydrofuran / 1.5 h / 0 °C

2: 70 percent / 18-crown-6 / acetonitrile / 16 h / Ambient temperature

With 18-crown-6 ether; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja00238a022

Reference yield:

[(3aS,5R,6aS,7aR,8R,9R,11aR,11bS,11cS)-3-(tert-Butyl-dimethyl-silanyloxy)-5-ethoxy-9-methoxy-8,11a-dimethyl-1,4,5,6a,7,7a,8,9,10,11,11a,11b-dodecahydro-3aH-6-oxa-benzo[de]anthracen-11c-yl]-methanol (105431-22-9) → 13,20-epoxy-16β-ethoxy-3β-methoxy-21-nitrilo-12β-(phenylseleno)-picrasane (105431-29-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

2: 80 percent / tetrahydrofuran / 1.5 h / 0 °C

3: 70 percent / 18-crown-6 / acetonitrile / 16 h / Ambient temperature

With 18-crown-6 ether; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja00238a022

upstream raw materials:

potassium cyanide

Methanesulfonic acid (2R,3aS,5R,6aS,7aR,8R,9R,11aR,11bS,11cS)-5-ethoxy-9-methoxy-8,11a-dimethyl-3-oxo-2-phenylselanyl-tetradecahydro-6-oxa-benzo[de]anthracen-11c-ylmethyl ester

Phenylselenyl chloride

[(3aS,5R,6aS,7aR,8R,9R,11aR,11bS,11cS)-3-(tert-Butyl-dimethyl-silanyloxy)-5-ethoxy-9-methoxy-8,11a-dimethyl-1,4,5,6a,7,7a,8,9,10,11,11a,11b-dodecahydro-3aH-6-oxa-benzo[de]anthracen-11c-yl]-methanol

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