Toluene-4-sulfonic acid 3-[(3aS,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-5-eth-(Z)-ylidene-2-oxo-hexahydro-cyclopentaoxazol-(4Z)-ylidene]-propyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 3-[(3aS,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-5-eth-(Z)-ylidene-2-oxo-hexahydro-cyclopentaoxazol-(4Z)-ylidene]-propyl ester
• CAS No.: 780769-13-3
• Molecular Formula: C₂₄H₃₅NO₆SSi
• Molecular Weight: 493.697
• Mol file: 780769-13-3.mol

Synonyms:Toluene-4-sulfonic acid 3-[(3aS,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-5-eth-(Z)-ylidene-2-oxo-hexahydro-cyclopentaoxazol-(4Z)-ylidene]-propyl ester

Chemical Property of Toluene-4-sulfonic acid 3-[(3aS,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-5-eth-(Z)-ylidene-2-oxo-hexahydro-cyclopentaoxazol-(4Z)-ylidene]-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid 3-[(3aS,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-5-eth-(Z)-ylidene-2-oxo-hexahydro-cyclopentaoxazol-(4Z)-ylidene]-propyl ester

There total 9 articles about Toluene-4-sulfonic acid 3-[(3aS,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-5-eth-(Z)-ylidene-2-oxo-hexahydro-cyclopentaoxazol-(4Z)-ylidene]-propyl 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: 64.0%

Toluene-4-sulfonic acid 4-{(4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-2-ynyl]-2-oxo-oxazolidin-4-yl}-but-3-ynyl ester (780769-12-2) → Toluene-4-sulfonic acid 3-[(3aS,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-5-eth-(Z)-ylidene-2-oxo-hexahydro-cyclopentaoxazol-(4Z)-ylidene]-propyl ester (780769-13-3)

Guidance literature:

With triethylsilane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; formic acid; In toluene; at 20 ℃; for 6h;

DOI:10.1002/anie.200460058

Reference yield:

(4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one (780769-10-0) → Toluene-4-sulfonic acid 3-[(3aS,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-5-eth-(Z)-ylidene-2-oxo-hexahydro-cyclopentaoxazol-(4Z)-ylidene]-propyl ester (780769-13-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 °C / Moffatt-Swern oxidation

1.2: 50 percent / zinc chloride / tetrahydrofuran / -78 - 2 °C

2.1: 75 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

3.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 0 - 20 °C

4.1: 75 percent / pyridine / 5 h / 20 °C

5.1: 64 percent / Pd₂(dba)3*CHCl₃; triethylsilane; formic acid / toluene / 6 h / 20 °C

With pyridine; 1H-imidazole; triethylsilane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; formic acid; oxalyl dichloride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; toluene;

DOI:10.1002/anie.200460058

Reference yield:

Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-pent-2-ynyl]-amine → Toluene-4-sulfonic acid 3-[(3aS,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-5-eth-(Z)-ylidene-2-oxo-hexahydro-cyclopentaoxazol-(4Z)-ylidene]-propyl ester (780769-13-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Pd(dba)2; 1,4-bis(diphenylphosphanyl)butane; 2-thiosalicylic acid / tetrahydrofuran / 0.67 h / 60 °C

1.2: 99 percent / aq. sodium bicarbonate / tetrahydrofuran / 0.5 h / 20 °C

2.1: p-toluenesulfonic acid monohydrate / methanol / 12 h

2.2: 88 percent / aq. potassium carbonate / methanol / 20 °C

3.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 °C / Moffatt-Swern oxidation

3.2: 50 percent / zinc chloride / tetrahydrofuran / -78 - 2 °C

4.1: 75 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

5.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 0 - 20 °C

6.1: 75 percent / pyridine / 5 h / 20 °C

7.1: 64 percent / Pd₂(dba)3*CHCl₃; triethylsilane; formic acid / toluene / 6 h / 20 °C

With pyridine; 1H-imidazole; triethylsilane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; formic acid; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; Thiosalicylic acid; triethylamine; 1,4-di(diphenylphosphino)-butane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1002/anie.200460058

upstream raw materials:

Toluene-4-sulfonic acid 4-{(4S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-2-ynyl]-2-oxo-oxazolidin-4-yl}-but-3-ynyl ester

(4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-(4-hydroxy-but-1-ynyl)-oxazolidin-2-one

(4S,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

Downstream raw materials:

(+)-streptazolin