(4S,6R,7R,8R,10S)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-7-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-10-ethylsulfanyl-8-((E)-oct-6-enyl)-5-oxo-bicyclo[4.3.1]dec-1⁽⁹⁾-ene-2,2-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (4S,6R,7R,8R,10S)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-7-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-10-ethylsulfanyl-8-((E)-oct-6-enyl)-5-oxo-bicyclo[4.3.1]dec-1⁽⁹⁾-ene-2,2-dicarboxylic acid dimethyl ester
• CAS No.: 298195-04-7
• Molecular Formula: C₄₆H₆₃NO₁₀S
• Molecular Weight: 822.073

Synonyms:(4S,6R,7R,8R,10S)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-7-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-10-ethylsulfanyl-8-((E)-oct-6-enyl)-5-oxo-bicyclo[4.3.1]dec-1⁽⁹⁾-ene-2,2-dicarboxylic acid dimethyl ester

Chemical Property of (4S,6R,7R,8R,10S)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-7-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-10-ethylsulfanyl-8-((E)-oct-6-enyl)-5-oxo-bicyclo[4.3.1]dec-1⁽⁹⁾-ene-2,2-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (4S,6R,7R,8R,10S)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-7-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-10-ethylsulfanyl-8-((E)-oct-6-enyl)-5-oxo-bicyclo[4.3.1]dec-1⁽⁹⁾-ene-2,2-dicarboxylic acid dimethyl ester

There total 8 articles about (4S,6R,7R,8R,10S)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-7-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-10-ethylsulfanyl-8-((E)-oct-6-enyl)-5-oxo-bicyclo[4.3.1]dec-1⁽⁹⁾-ene-2,2-dicarboxylic acid dimethyl ester 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-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester (298195-03-6) → (4S,6R,7R,8R,10S)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-7-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-10-ethylsulfanyl-8-((E)-oct-6-enyl)-5-oxo-bicyclo[4.3.1]dec-1(9)-ene-2,2-dicarboxylic acid dimethyl ester (298195-04-7)

Guidance literature:

With zinc chloride diethyl ether; In dichloromethane; for 1h;

DOI:10.1021/ja001664b

Reference yield:

(S)-3-acryloyl-4-benzyloxazolidin-2-one (90719-27-0) → (4S,6R,7R,8R,10S)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-7-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-10-ethylsulfanyl-8-((E)-oct-6-enyl)-5-oxo-bicyclo[4.3.1]dec-1(9)-ene-2,2-dicarboxylic acid dimethyl ester (298195-04-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Cs₂CO₃ / acetonitrile / 50 °C

2: 80 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: 75 percent / SO₃*Py; i-Pr₂NEt / dimethylsulfoxide / 1 h

4: ZnCl₂*OEt₂ / CH₂Cl₂ / 1 h

With zinc chloride diethyl ether; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; acetonitrile; 1: Michael addition / 3: Parikh-Doering oxidation / 4: Diels-Alder reaction;

DOI:10.1021/ja001664b

Reference yield:

4-Ethylsulfanyl-but-2-ynoic acid methyl ester → (4S,6R,7R,8R,10S)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-7-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-10-ethylsulfanyl-8-((E)-oct-6-enyl)-5-oxo-bicyclo[4.3.1]dec-1(9)-ene-2,2-dicarboxylic acid dimethyl ester (298195-04-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DBU / tetrahydrofuran / 0 °C

1.2: 80 percent / TMSCl; HMPA; Me₂S*THF / -78 - 20 °C

2.1: 84 percent / LHMDS / tetrahydrofuran / -78 °C

3.1: 82 percent / Cs₂CO₃ / acetonitrile / 50 °C

4.1: 80 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

5.1: 75 percent / SO₃*Py; i-Pr₂NEt / dimethylsulfoxide / 1 h

6.1: ZnCl₂*OEt₂ / CH₂Cl₂ / 1 h

With zinc chloride diethyl ether; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; 3.1: Michael addition / 5.1: Parikh-Doering oxidation / 6.1: Diels-Alder reaction;

DOI:10.1021/ja001664b

upstream raw materials:

2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

(S)-3-acryloyl-4-benzyloxazolidin-2-one

(4E,11E)-3-[1-Ethylsulfanyl-meth-(E)-ylidene]-trideca-4,11-dienoic acid methyl ester

2-{(2E,9E)-1-[1-Ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

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