methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate

Base Information

• Chemical Name: methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate
• CAS No.: 1609534-04-4
• Molecular Formula: C₂₆H₃₀ClNO₄
• Molecular Weight: 455.982

Synonyms:methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate

Chemical Property of methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate

There total 8 articles about methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate 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: 30.0%

methyl (6E,10Z)-(12S)-12-benzyloxy-2-chloro-10-cyano-6-methyl-3-oxohexadeca-6,10,15-trienoate (1609534-02-2) → methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate (1609534-04-4) + methyl (4aS,4bS,5S,8aR,10aS)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate

Guidance literature:

With copper(II) acetate monohydrate; manganese(III) triacetate dihydrate; In ethanol; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.04.018

Reference yield:

(R)-2-((S)-1-(benzyloxy)pent-4-enyl)-1,4-dioxaspiro[4.5]decane (1554519-01-5) → methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate (1609534-04-4)

Guidance literature:

Multi-step reaction with 6 steps

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

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

2.2: 0.17 h / -78 °C / Inert atmosphere

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

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

4.2: 3 h / 20 °C / Inert atmosphere

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

5.2: 3 h / 40 °C / Inert atmosphere

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

With hydrogenchloride; sodium periodate; n-butyllithium; copper(II) acetate monohydrate; manganese(III) triacetate dihydrate; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; Methanesulfonic anhydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile; mineral oil;

DOI:10.1016/j.tetlet.2014.04.018

Reference yield:

(S)-1-((R)-1,4-dioxaspiro[4.5]decan-2-yl)pent-4-en-1-ol (113730-85-1) → methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate (1609534-04-4)

Guidance literature:

Multi-step reaction with 7 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

With hydrogenchloride; sodium periodate; n-butyllithium; copper(II) acetate monohydrate; manganese(III) triacetate dihydrate; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; Methanesulfonic anhydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 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

(R)-2-((S)-1-(benzyloxy)pent-4-enyl)-1,4-dioxaspiro[4.5]decane

(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

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

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