(4S)-4-[N-(Ac-Asp(O-tBu)-D-Glu(O-tBu)-Leu-Ile-Cha)-amino]-1-(thiazol-2-yl)-1-hexen-3-one

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Chemical Name:(4S)-4-[N-(Ac-Asp(O-tBu)-D-Glu(O-tBu)-Leu-Ile-Cha)-amino]-1-(thiazol-2-yl)-1-hexen-3-one
CAS No.:622841-19-4
Molecular Formula:C₄₉H₇₉N₇O₁₁S
Molecular Weight:974.273
Hs Code.:

Synonyms:(4S)-4-[N-(Ac-Asp(O-tBu)-D-Glu(O-tBu)-Leu-Ile-Cha)-amino]-1-(thiazol-2-yl)-1-hexen-3-one

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Chemical Property of (4S)-4-[N-(Ac-Asp(O-tBu)-D-Glu(O-tBu)-Leu-Ile-Cha)-amino]-1-(thiazol-2-yl)-1-hexen-3-one

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Technology Process of (4S)-4-[N-(Ac-Asp(O-tBu)-D-Glu(O-tBu)-Leu-Ile-Cha)-amino]-1-(thiazol-2-yl)-1-hexen-3-one

There total 4 articles about (4S)-4-[N-(Ac-Asp(O-tBu)-D-Glu(O-tBu)-Leu-Ile-Cha)-amino]-1-(thiazol-2-yl)-1-hexen-3-one 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: 72.0%

: 622841-14-9
(4S)-4-[N-(Ac-Asp(O-tBu)-D-Glu(O-tBu)-Leu-Ile-Cha)-amino]-3-hydroxy-1-(thiazol-2-yl)-1-hexene

: 622841-19-4
(4S)-4-[N-(Ac-Asp(O-tBu)-D-Glu(O-tBu)-Leu-Ile-Cha)-amino]-1-(thiazol-2-yl)-1-hexen-3-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1016/S0968-0896(03)00190-1

Reference yield:

: 71989-23-6,251316-98-0
Fmoc-Ile-OH

: 622841-19-4
(4S)-4-[N-(Ac-Asp(O-tBu)-D-Glu(O-tBu)-Leu-Ile-Cha)-amino]-1-(thiazol-2-yl)-1-hexen-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: 164 mg / PyBOP; DIPEA / CH₂Cl₂ / 16 h

2: 72 percent / Dess-Martin reagent / CH₂Cl₂ / 16 h / 20 °C

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In dichloromethane; 3: Dess-Martin oxidation;
DOI:10.1016/S0968-0896(03)00190-1

Reference yield:

: 622841-44-5
(3-tert-butoxycarbonylamino-2-oxo-pentyl)-phosphonic acid dimethyl ester

: 622841-19-4
(4S)-4-[N-(Ac-Asp(O-tBu)-D-Glu(O-tBu)-Leu-Ile-Cha)-amino]-1-(thiazol-2-yl)-1-hexen-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / K₂CO₃ / ethanol / 16 h

2: 76 percent / NaBH₄ / methanol / 2.5 h / 0 °C

3: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 6 h

4: 164 mg / PyBOP; DIPEA / CH₂Cl₂ / 16 h

5: 72 percent / Dess-Martin reagent / CH₂Cl₂ / 16 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; dichloromethane; 1: Horner-Wadsworth-Emmons reaction / 5: Dess-Martin oxidation;
DOI:10.1016/S0968-0896(03)00190-1