methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1,2-epoxy-3-hydroxypropyl]-thiazole-4-carboxylate

Base Information

• Chemical Name: methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1,2-epoxy-3-hydroxypropyl]-thiazole-4-carboxylate
• CAS No.: 1389271-18-4
• Molecular Formula: C₁₆H₁₅NO₆S
• Molecular Weight: 349.364
• Mol file: 1389271-18-4.mol

Synonyms:methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1,2-epoxy-3-hydroxypropyl]-thiazole-4-carboxylate

Chemical Property of methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1,2-epoxy-3-hydroxypropyl]-thiazole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1,2-epoxy-3-hydroxypropyl]-thiazole-4-carboxylate

There total 9 articles about methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1,2-epoxy-3-hydroxypropyl]-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: 42.0%

methyl 2-[(1R,2R,3S)-3-(benzyloxycarbonyl)-1-methanesulfonyloxy-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate (1389271-16-2) → methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1,2-epoxy-3-hydroxypropyl]-thiazole-4-carboxylate (1389271-18-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.75h; Inert atmosphere;

DOI:10.1016/j.tet.2012.06.022

Reference yield:

D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) → methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1,2-epoxy-3-hydroxypropyl]-thiazole-4-carboxylate (1389271-18-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium periodate; disodium hydrogenphosphate / water / 1 h / 0 °C

2.1: pyridine / methanol; water / 15 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere

4.1: manganese(IV) oxide / toluene / 79 h / 70 °C

5.1: camphor-10-sulfonic acid / 67 h / 50 °C

6.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 1.5 h / 80 °C

8.1: boron trifluoride diethyl etherate; tri-n-butyl-tin hydride / toluene / -78 - 20 °C / Inert atmosphere

8.2: 4 h / 20 °C / Inert atmosphere

9.1: pyridine; dmap / 0 - 20 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; sodium periodate; disodium hydrogenphosphate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2012.06.022

Reference yield:

methyl 2-[((2S,3S,4S)-3,4-bis[(triethylsilyl)oxy]-5-oxo-tetrahydrofuran-2-yl)]-thiazole-4-carboxylate (1389271-06-0) → methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1,2-epoxy-3-hydroxypropyl]-thiazole-4-carboxylate (1389271-18-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: camphor-10-sulfonic acid / 67 h / 50 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 1.5 h / 80 °C

4.1: boron trifluoride diethyl etherate; tri-n-butyl-tin hydride / toluene / -78 - 20 °C / Inert atmosphere

4.2: 4 h / 20 °C / Inert atmosphere

5.1: pyridine; dmap / 0 - 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2012.06.022

upstream raw materials:

D-glucurono-6,3-lactone

methyl 2-[(1R,2S,3S)-3-(benzyloxycarbonyl)-1,2-dihydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate

methyl 2-[(1R,2R,3S)-3-(benzyloxycarbonyl)-1-methanesulfonyloxy-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate

(2S,4R)-methyl 2-[((2S,3R,4S)-3,4-dihydroxy-5-oxo-tetrahydrofuran-2-yl)]-thiazolidine-4-carboxylate