(+)-(1R,2S,6S,7S)-N-[(2'R)-2'-benzyl-3'-ethoxycarbonylpropionyl]-3,4-thiazatricyclo[5.2.1.0^2,6]deca-8-ene-3,3-dioxide

Base Information

• Chemical Name: (+)-(1R,2S,6S,7S)-N-[(2'R)-2'-benzyl-3'-ethoxycarbonylpropionyl]-3,4-thiazatricyclo[5.2.1.0^2,6]deca-8-ene-3,3-dioxide
• CAS No.: 256509-00-9
• Molecular Formula: C₂₁H₂₅NO₅S
• Molecular Weight: 403.499
• Mol file: 256509-00-9.mol

Synonyms:

Chemical Property of (+)-(1R,2S,6S,7S)-N-[(2'R)-2'-benzyl-3'-ethoxycarbonylpropionyl]-3,4-thiazatricyclo[5.2.1.0^2,6]deca-8-ene-3,3-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1R,2S,6S,7S)-N-[(2'R)-2'-benzyl-3'-ethoxycarbonylpropionyl]-3,4-thiazatricyclo[5.2.1.0^2,6]deca-8-ene-3,3-dioxide

There total 3 articles about (+)-(1R,2S,6S,7S)-N-[(2'R)-2'-benzyl-3'-ethoxycarbonylpropionyl]-3,4-thiazatricyclo[5.2.1.0^2,6]deca-8-ene-3,3-dioxide 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:

ethyl bromoacetate (105-36-2) + (-)-(1S,2R,6R,7R)-N-butanoyl-3,4-thiazatricyclo[5.2.1.02,6]deca-8-ene-3,3-dioxide (256508-94-8) → (S)-3-Benzyl-4-((1R,2S,6S,7S)-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl)-4-oxo-butyric acid ethyl ester + (+)-(1R,2S,6S,7S)-N-[(2'R)-2'-benzyl-3'-ethoxycarbonylpropionyl]-3,4-thiazatricyclo[5.2.1.02,6]deca-8-ene-3,3-dioxide (256509-00-9)

Guidance literature:

(-)-(1S,2R,6R,7R)-N-butanoyl-3,4-thiazatricyclo[5.2.1.0^2,6]deca-8-ene-3,3-dioxide; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

ethyl bromoacetate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 16h;

DOI:10.1016/S0040-4020(99)00872-8

Reference yield:

hydrocinnamic acid chloride (645-45-4) → (+)-(1R,2S,6S,7S)-N-[(2'R)-2'-benzyl-3'-ethoxycarbonylpropionyl]-3,4-thiazatricyclo[5.2.1.02,6]deca-8-ene-3,3-dioxide (256509-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C

1.2: 82 percent / tetrahydrofuran; hexane / 2 h / 20 °C

2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: hexamethylphosphoric acid triamide; tetrahydrofuran / 16 h / -78 °C

With n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexane; 1.1: Metallation / 1.2: Acylation / 2.1: Metallation / 2.2: Alkylation;

DOI:10.1016/S0040-4020(99)00872-8

Reference yield:

(1S,2R,6R,7R)-3-Thia-4-aza-tricyclo[5.2.1.02,6]dec-8-ene 3,3-dioxide (197080-12-9) → (+)-(1R,2S,6S,7S)-N-[(2'R)-2'-benzyl-3'-ethoxycarbonylpropionyl]-3,4-thiazatricyclo[5.2.1.02,6]deca-8-ene-3,3-dioxide (256509-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C

1.2: 82 percent / tetrahydrofuran; hexane / 2 h / 20 °C

2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: hexamethylphosphoric acid triamide; tetrahydrofuran / 16 h / -78 °C

With n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexane; 1.1: Metallation / 1.2: Acylation / 2.1: Metallation / 2.2: Alkylation;

DOI:10.1016/S0040-4020(99)00872-8

upstream raw materials:

ethyl bromoacetate

(-)-(1S,2R,6R,7R)-N-butanoyl-3,4-thiazatricyclo[5.2.1.0^2,6]deca-8-ene-3,3-dioxide

hydrocinnamic acid chloride

(1S,2R,6R,7R)-3-Thia-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene 3,3-dioxide

Downstream raw materials:

(R)-2-benzyl-butan-1,4-diol