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

Base Information

Chemical Name:methyl 2-[(1R,2S,3S)-3-(benzyloxycarbonyl)-1,2-dihydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate
CAS No.:1389271-15-1
Molecular Formula:C₂₂H₃₁NO₇SSi
Molecular Weight:481.642
Hs Code.:

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

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

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

There total 7 articles about methyl 2-[(1R,2S,3S)-3-(benzyloxycarbonyl)-1,2-dihydroxy-3-(tert-butyl-dimethylsilyloxy)-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: 75.0%

: 1389271-13-9
methyl 2-[(2R,3S)-3-(benzyloxycarbonyl)-1-oxo-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate

: 1389271-15-1
methyl 2-[(1R,2S,3S)-3-(benzyloxycarbonyl)-1,2-dihydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate

Guidance literature:: methyl 2-[(2R,3S)-3-(benzyloxycarbonyl)-1-oxo-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate; With boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; In toluene; at -78 - 20 ℃; Inert atmosphere;

With water; sodium hydrogencarbonate; In toluene; at 20 ℃; for 4h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2012.06.022

Reference yield:

: 63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2
D-glucurono-6,3-lactone

: 1389271-15-1
methyl 2-[(1R,2S,3S)-3-(benzyloxycarbonyl)-1,2-dihydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 8 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

With pyridine; 1H-imidazole; manganese(IV) oxide; sodium periodate; disodium hydrogenphosphate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2012.06.022

Reference yield:

: 1389271-06-0
methyl 2-[((2S,3S,4S)-3,4-bis[(triethylsilyl)oxy]-5-oxo-tetrahydrofuran-2-yl)]-thiazole-4-carboxylate

: 1389271-15-1
methyl 2-[(1R,2S,3S)-3-(benzyloxycarbonyl)-1,2-dihydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2012.06.022