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

Base Information

• Chemical Name: (-)-(1S,2R,6R,7R)-N-butanoyl-3,4-thiazatricyclo[5.2.1.0^2,6]deca-8-ene-3,3-dioxide
• CAS No.: 256508-94-8
• Molecular Formula: C₁₇H₁₉NO₃S
• Molecular Weight: 317.409

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

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

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

There total 1 articles about (-)-(1S,2R,6R,7R)-N-butanoyl-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: 82.0%

hydrocinnamic acid chloride (645-45-4) + (1S,2R,6R,7R)-3-Thia-4-aza-tricyclo[5.2.1.02,6]dec-8-ene 3,3-dioxide (197080-12-9) → (-)-(1S,2R,6R,7R)-N-butanoyl-3,4-thiazatricyclo[5.2.1.02,6]deca-8-ene-3,3-dioxide (256508-94-8)

Guidance literature:

(1S,2R,6R,7R)-3-Thia-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene 3,3-dioxide; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

hydrocinnamic acid chloride; In tetrahydrofuran; hexane; at 20 ℃; for 2h;

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

Reference yield: 63.0%

Ethyl 2-bromopropionate (535-11-5,41978-69-2) + (-)-(1S,2R,6R,7R)-N-butanoyl-3,4-thiazatricyclo[5.2.1.02,6]deca-8-ene-3,3-dioxide (256508-94-8) → (-)-(1R,2S,6S,7S)-N-[(2'R),(3'R)-2'-benzyl-3'-methyl-3'-ethoxycarbonylpropionyl]-3,4-thiazatricyclo[5.2.1.02,6]deca-8-ene-3,3-dioxide

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 2-bromopropionate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 20h;

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

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

upstream raw materials:

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:

(+)-(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

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