(1S,4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-4a-methyl-8-methylene-2-oxoperhydro-phenanthrene-8a-carbonitrile

Base Information

• Chemical Name: (1S,4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-4a-methyl-8-methylene-2-oxoperhydro-phenanthrene-8a-carbonitrile
• CAS No.: 1609534-05-5
• Molecular Formula: C₂₄H₂₈ClNO₂
• Molecular Weight: 397.945
• Mol file: 1609534-05-5.mol

Synonyms:(1S,4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-4a-methyl-8-methylene-2-oxoperhydro-phenanthrene-8a-carbonitrile

Chemical Property of (1S,4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-4a-methyl-8-methylene-2-oxoperhydro-phenanthrene-8a-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-4a-methyl-8-methylene-2-oxoperhydro-phenanthrene-8a-carbonitrile

There total 7 articles about (1S,4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-4a-methyl-8-methylene-2-oxoperhydro-phenanthrene-8a-carbonitrile 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:

(S)-1-((R)-1,4-dioxaspiro[4.5]decan-2-yl)pent-4-en-1-ol (113730-85-1) → (1S,4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-4a-methyl-8-methylene-2-oxoperhydro-phenanthrene-8a-carbonitrile (1609534-05-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 20 °C

2.1: hydrogenchloride / methanol; water / 15 h / 40 °C

3.1: sodium periodate / water; acetonitrile / 2 h / 0 °C

3.2: 0.17 h / -78 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / methanol / 13 h / 20 °C

5.1: triethylamine; Methanesulfonic anhydride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

5.2: 3 h / 20 °C / Inert atmosphere

6.1: sodium hydride; n-butyllithium / mineral oil; tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

6.2: 3 h / 40 °C / Inert atmosphere

7.1: manganese(III) triacetate dihydrate; copper(II) acetate monohydrate / ethanol / 4 h / 20 °C / Inert atmosphere

8.1: 2,6-di-tert-butyl-4-methyl-phenol; sodium chloride / water; dimethyl sulfoxide / 2 h / 150 °C

With hydrogenchloride; sodium periodate; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; copper(II) acetate monohydrate; manganese(III) triacetate dihydrate; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; sodium chloride; Methanesulfonic anhydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1016/j.tetlet.2014.04.018

Reference yield:

(2R,3S)-3-(benzyloxy)hept-6-ene-1,2-diol (1554519-04-8) → (1S,4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-4a-methyl-8-methylene-2-oxoperhydro-phenanthrene-8a-carbonitrile (1609534-05-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium periodate / water; acetonitrile / 2 h / 0 °C

1.2: 0.17 h / -78 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / methanol / 13 h / 20 °C

3.1: triethylamine; Methanesulfonic anhydride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

3.2: 3 h / 20 °C / Inert atmosphere

4.1: sodium hydride; n-butyllithium / mineral oil; tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

4.2: 3 h / 40 °C / Inert atmosphere

5.1: manganese(III) triacetate dihydrate; copper(II) acetate monohydrate / ethanol / 4 h / 20 °C / Inert atmosphere

6.1: 2,6-di-tert-butyl-4-methyl-phenol; sodium chloride / water; dimethyl sulfoxide / 2 h / 150 °C

With sodium periodate; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; copper(II) acetate monohydrate; manganese(III) triacetate dihydrate; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; sodium chloride; Methanesulfonic anhydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile; mineral oil;

DOI:10.1016/j.tetlet.2014.04.018

Reference yield:

[(E)-1-Cyano-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyl]-phosphonic acid diethyl ester (202338-89-4) → (1S,4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-4a-methyl-8-methylene-2-oxoperhydro-phenanthrene-8a-carbonitrile (1609534-05-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium periodate / water; acetonitrile / 2 h / 0 °C

1.2: 0.17 h / -78 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / methanol / 13 h / 20 °C

3.1: triethylamine; Methanesulfonic anhydride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

3.2: 3 h / 20 °C / Inert atmosphere

4.1: sodium hydride; n-butyllithium / mineral oil; tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

4.2: 3 h / 40 °C / Inert atmosphere

5.1: manganese(III) triacetate dihydrate; copper(II) acetate monohydrate / ethanol / 4 h / 20 °C / Inert atmosphere

6.1: 2,6-di-tert-butyl-4-methyl-phenol; sodium chloride / water; dimethyl sulfoxide / 2 h / 150 °C

With sodium periodate; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; copper(II) acetate monohydrate; manganese(III) triacetate dihydrate; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; sodium chloride; Methanesulfonic anhydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile; mineral oil;

DOI:10.1016/j.tetlet.2014.04.018

upstream raw materials:

(S)-1-((R)-1,4-dioxaspiro[4.5]decan-2-yl)pent-4-en-1-ol

(2R,3S)-3-(benzyloxy)hept-6-ene-1,2-diol

[(E)-1-Cyano-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyl]-phosphonic acid diethyl ester

(2Z)-(4S)-4-benzyloxy-2-[(E)-4-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-enyl]octa-2,7-dienenitrile

Downstream raw materials:

(4aR,4bR,5S,8aS)-5-benzyloxy-4a-methyl-8-methylene-2-oxo-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthrene-8a-carbonitrile