ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-dihydroxybutyl>thiazole-4-carboxylate

Base Information

Chemical Name:ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-dihydroxybutyl>thiazole-4-carboxylate
CAS No.:173259-15-9
Molecular Formula:C₂₄H₃₆N₂O₆SSi
Molecular Weight:508.711
Hs Code.:

Synonyms:ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-dihydroxybutyl>thiazole-4-carboxylate

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Chemical Property of ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-dihydroxybutyl>thiazole-4-carboxylate

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Technology Process of ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-dihydroxybutyl>thiazole-4-carboxylate

There total 9 articles about ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-dihydroxybutyl>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: 95.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 173259-14-8
ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-3,4-dihydroxybutyl>thiazole-4-carboxylate

: 173259-15-9
ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-dihydroxybutyl>thiazole-4-carboxylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1246/bcsj.68.3151

Reference yield:

: 70-23-5
ethyl Bromopyruvate

: 173259-15-9
ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-dihydroxybutyl>thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) KHCO₃, 2.) trifluoroacetic anhydride, pyridine / 1.) DME, 0 deg C, 10 min, 2.) DME, 2 h

2: 93 percent / 70percent AcOH / Ambient temperature

3: 95 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; dmap; potassium hydrogencarbonate; acetic acid; triethylamine; trifluoroacetic anhydride; In dichloromethane;
DOI:10.1246/bcsj.68.3151

Reference yield:

: 114684-69-4
methyl 2-(benzyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetate

: 173259-15-9
ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-dihydroxybutyl>thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) 5percent aq. NaHCO₃, aq. NaIO₄, 2.) 6 M aq. K₂CO₃, tetrabutylammonium bromide / 1.) 1 h, 2.) CH₂Cl₂, RT, 4 h

2: 84 percent / NaBH₄, NiCl₂*6H₂O / methanol / 1 h / Ambient temperature

3: 43 percent / CaCl2 / 20 h / 35 °C / α-chymotrypsin

4: 1.) dicyclohexylcarbodiimide, 2.) N-hydroxysuccinimide, 3.) aq. NH₃

5: 65 percent / Lawesson's reagent / 1,2-dimethoxy-ethane / 0 °C

6: 1.) KHCO₃, 2.) trifluoroacetic anhydride, pyridine / 1.) DME, 0 deg C, 10 min, 2.) DME, 2 h

7: 93 percent / 70percent AcOH / Ambient temperature

8: 95 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / 0 °C

With Lawessons reagent; pyridine; dmap; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; 1-hydroxy-pyrrolidine-2,5-dione; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium carbonate; potassium hydrogencarbonate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; calcium chloride; nickel dichloride; In methanol; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1246/bcsj.68.3151