ethyl 2-(3-acetamido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)thiazole-4-carboxylate

Base Information

Chemical Name:ethyl 2-(3-acetamido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)thiazole-4-carboxylate
CAS No.:615249-54-2
Molecular Formula:C₂₇H₂₆N₂O₈S
Molecular Weight:538.578
Hs Code.:

Synonyms:ethyl 2-(3-acetamido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)thiazole-4-carboxylate

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Chemical Property of ethyl 2-(3-acetamido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)thiazole-4-carboxylate

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Technology Process of ethyl 2-(3-acetamido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)thiazole-4-carboxylate

There total 9 articles about ethyl 2-(3-acetamido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)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: 37.0%

: 70-23-5
ethyl Bromopyruvate

: 615249-53-1
4-acetamido-2,5-anhydro-3,6-di-O-benzoyl-4-deoxy-D-gulono-thioamide

: 615249-54-2
ethyl 2-(3-acetamido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)thiazole-4-carboxylate

Guidance literature:: In ethanol; at 80 ℃; for 0.833333h;
DOI:10.1016/S0960-894X(03)00712-1

Reference yield:

: C₂₇H₂₈N₂O₈S

: 615249-54-2
ethyl 2-(3-acetamido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)thiazole-4-carboxylate

Guidance literature:: With Bromotrichloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 4 ℃;
DOI:10.1016/j.ejmech.2019.111712

Reference yield:

: 228399-13-1
2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulose ethylene acetal

: 615249-54-2
ethyl 2-(3-acetamido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 56 percent / PtO₂; AcOH / 21 h / 20 °C

2: TFA; aq. HCl / 144 h / 4 °C

3: NH₂OH*HCl; NaOAc / ethanol / 72 h / 4 - 20 °C

4: MsCl; pyridine / 2 h / -15 - 20 °C

5: 81 percent / H₂S; DMAP / ethanol / 4 h / 20 °C

6: 37 percent / ethanol / 0.83 h / 80 °C

With pyridine; hydrogenchloride; dmap; platinum(IV) oxide; hydrogen sulfide; hydroxylamine hydrochloride; sodium acetate; acetic acid; methanesulfonyl chloride; trifluoroacetic acid; In ethanol; 6: Hantzsch reaction;
DOI:10.1016/S0960-894X(03)00712-1