methyl 2-[(1S,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2,3-dihydroxypropyl]-thiazole-4-carboxylate

Base Information

• Chemical Name: methyl 2-[(1S,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2,3-dihydroxypropyl]-thiazole-4-carboxylate
• CAS No.: 1389270-98-7
• Molecular Formula: C₁₆H₁₆N₄O₆S
• Molecular Weight: 392.392
• Mol file: 1389270-98-7.mol

Synonyms:methyl 2-[(1S,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2,3-dihydroxypropyl]-thiazole-4-carboxylate

Chemical Property of methyl 2-[(1S,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2,3-dihydroxypropyl]-thiazole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-[(1S,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2,3-dihydroxypropyl]-thiazole-4-carboxylate

There total 17 articles about methyl 2-[(1S,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2,3-dihydroxypropyl]-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: 16.0%

methyl 2-[(1R,2R,3S)-3-(benzyloxycarbonyl)-1,2-epoxy-3-hydroxypropyl]-thiazole-4-carboxylate (1389271-24-2) → methyl 2-[(1S,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2,3-dihydroxypropyl]-thiazole-4-carboxylate (1389270-98-7)

Guidance literature:

With sodium azide; toluene-4-sulfonic acid; In water; dimethyl sulfoxide; at 70 ℃; for 9h; Inert atmosphere;

DOI:10.1016/j.tet.2012.06.022

Reference yield:

methyl 2-[(1R,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate (1389271-17-3) → methyl 2-[(1R,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2,3-dihydroxypropyl]-thiazole-4-carboxylate (1389271-01-5) + methyl 2-[(1S,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2,3-dihydroxypropyl]-thiazole-4-carboxylate (1389270-98-7)

Guidance literature:

With fluorosilicic acid; In acetonitrile; at 20 ℃; for 24h;

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,2S,3S)-3-(benzyloxycarbonyl)-1-azido-2,3-dihydroxypropyl]-thiazole-4-carboxylate (1389270-98-7)

Guidance literature:

Multi-step reaction with 9 steps

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

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

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

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

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

6: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C

7: pyridine / 0 - 20 °C / Inert atmosphere

8: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

9: sodium azide; toluene-4-sulfonic acid / water; dimethyl sulfoxide / 9 h / 70 °C / Inert atmosphere

With pyridine; 1H-imidazole; manganese(IV) oxide; sodium periodate; disodium hydrogenphosphate; sodium azide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; 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

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