But-2-ynoic acid (E)-(S)-1-(4-benzyloxymethyl-thiazol-2-ylmethyl)-3-bromo-but-2-enyl ester

Base Information

Chemical Name:But-2-ynoic acid (E)-(S)-1-(4-benzyloxymethyl-thiazol-2-ylmethyl)-3-bromo-but-2-enyl ester
CAS No.:218782-97-9
Molecular Formula:C₂₀H₂₀BrNO₃S
Molecular Weight:434.354
Hs Code.:

Synonyms:But-2-ynoic acid (E)-(S)-1-(4-benzyloxymethyl-thiazol-2-ylmethyl)-3-bromo-but-2-enyl ester

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Chemical Property of But-2-ynoic acid (E)-(S)-1-(4-benzyloxymethyl-thiazol-2-ylmethyl)-3-bromo-but-2-enyl ester

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Technology Process of But-2-ynoic acid (E)-(S)-1-(4-benzyloxymethyl-thiazol-2-ylmethyl)-3-bromo-but-2-enyl ester

There total 9 articles about But-2-ynoic acid (E)-(S)-1-(4-benzyloxymethyl-thiazol-2-ylmethyl)-3-bromo-but-2-enyl 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:

: 590-93-2
2-Butynoic acid

: 218782-96-8
(E)-(R)-1-(4-Benzyloxymethyl-thiazol-2-yl)-4-bromo-pent-3-en-2-ol

: 218782-97-9
But-2-ynoic acid (E)-(S)-1-(4-benzyloxymethyl-thiazol-2-ylmethyl)-3-bromo-but-2-enyl ester

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -20 ℃;
DOI:10.1021/ja981846u

Reference yield:

: 201339-99-3
(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enoic acid amide

: 218782-97-9
But-2-ynoic acid (E)-(S)-1-(4-benzyloxymethyl-thiazol-2-ylmethyl)-3-bromo-but-2-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / (PhOPh)2P₂S₄ / tetrahydrofuran / 0.5 h / 25 °C

2: KHCO₃ / 1,2-dimethoxy-ethane / -30 - 25 °C

3: trifluoroacetic anhydride, 2,6-lutidine / 1,2-dimethoxy-ethane / 1 h / -30 °C

4: DIBAL-H

5: NaH

6: TBAF

7: DIAD, Ph₃P / tetrahydrofuran / -20 °C

With 2,6-dimethylpyridine; di-isopropyl azodicarboxylate; (PhOPh)2P₂S₄; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; potassium hydrogencarbonate; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; 1,2-dimethoxyethane;
DOI:10.1021/ja981846u

Reference yield:

: 218782-63-9
(E)-(R)-5-Bromo-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-hex-4-en-1-one

: 218782-97-9
But-2-ynoic acid (E)-(S)-1-(4-benzyloxymethyl-thiazol-2-ylmethyl)-3-bromo-but-2-enyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / 0 - 20 °C

2: 90 percent / NH₃ gas / CH₂Cl₂ / 0 °C

3: 72 percent / (PhOPh)2P₂S₄ / tetrahydrofuran / 0.5 h / 25 °C

4: KHCO₃ / 1,2-dimethoxy-ethane / -30 - 25 °C

5: trifluoroacetic anhydride, 2,6-lutidine / 1,2-dimethoxy-ethane / 1 h / -30 °C

6: DIBAL-H

7: NaH

8: TBAF

9: DIAD, Ph₃P / tetrahydrofuran / -20 °C

With 2,6-dimethylpyridine; di-isopropyl azodicarboxylate; (PhOPh)2P₂S₄; tetrabutyl ammonium fluoride; ammonia; sodium hydride; diisobutylaluminium hydride; potassium hydrogencarbonate; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/ja981846u