methyl 2-<(1S,3S)-1-t-butoxycarbonylamino-3-ethoxycarbonyl-3-(methoxymethoxy)propyl>thiazole-4-carboxylate

Base Information

• Chemical Name: methyl 2-<(1S,3S)-1-t-butoxycarbonylamino-3-ethoxycarbonyl-3-(methoxymethoxy)propyl>thiazole-4-carboxylate
• CAS No.: 173259-03-5
• Molecular Formula: C₁₈H₂₈N₂O₈S
• Molecular Weight: 432.495

Synonyms:methyl 2-<(1S,3S)-1-t-butoxycarbonylamino-3-ethoxycarbonyl-3-(methoxymethoxy)propyl>thiazole-4-carboxylate

Chemical Property of methyl 2-<(1S,3S)-1-t-butoxycarbonylamino-3-ethoxycarbonyl-3-(methoxymethoxy)propyl>thiazole-4-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of methyl 2-<(1S,3S)-1-t-butoxycarbonylamino-3-ethoxycarbonyl-3-(methoxymethoxy)propyl>thiazole-4-carboxylate

There total 1 articles about methyl 2-<(1S,3S)-1-t-butoxycarbonylamino-3-ethoxycarbonyl-3-(methoxymethoxy)propyl>thiazole-4-carboxylate 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:

(S)-Pyroglutaminol (17342-08-4) → methyl 2-<(1S,3S)-1-t-butoxycarbonylamino-3-ethoxycarbonyl-3-(methoxymethoxy)propyl>thiazole-4-carboxylate (173259-03-5)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole / dimethylformamide / Ambient temperature

2: Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

3: 1.) 1,1,1,3,3,3-hexamethyldisilazane, n-BuLi, 2.) oxodiperoxo(pyridine)molybdenum(VI)-hexamethylphosphoric triamide / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, -40 deg C

4: 78 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran; benzene / 5 h / 0 °C

5: 89 percent / ethanol / 0 °C

6: 96 percent / (i-Pr)2NEt / CH₂Cl₂ / 6 h / Ambient temperature

7: 80 percent / n-Bu₄NF, AcOH / tetrahydrofuran / 8 h / Ambient temperature

8: 1.) pyridine*SO₃, DMSO, Et₃N / 1.) CH₂Cl₂, -10 deg C, 2 h, 2.) benzene, RT, overnight

9: MnO₂, pyridine / benzene / Irradiation

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; n-butyllithium; MoO₅*pyridine*HMPA; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1246/bcsj.68.3151

upstream raw materials:

(S)-Pyroglutaminol

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