3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-tert-butyldimethylsilyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole

Base Information

Chemical Name:3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-tert-butyldimethylsilyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole
CAS No.:1384188-40-2
Molecular Formula:C₂₆H₃₁ClN₂O₆SSi
Molecular Weight:563.146
Hs Code.:

Synonyms:3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-tert-butyldimethylsilyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole

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Chemical Property of 3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-tert-butyldimethylsilyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole

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Technology Process of 3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-tert-butyldimethylsilyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole

There total 3 articles about 3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-tert-butyldimethylsilyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole 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: 25.4%

: 1384188-38-8
6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-α-D-xylo-hexofuranos-5-ulose

: 569350-52-3
N'-[5-(4-chlorobenzoyl)-1,3-thiazol-2-yl]-N,N-dimethylimidoformamide

: 1384188-40-2
3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-tert-butyldimethylsilyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole

Guidance literature:: 6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-(tert-butyldimethylsilyl)-α-D-xylo-hexofuranos-5-ulose; N'-[5-(4-chlorobenzoyl)-1,3-thiazol-2-yl]-N,N-dimethylimidoformamide; In tetrahydrofuran; at 105 ℃; for 2.5h; Microwave irradiation;

With triethylamine; In tetrahydrofuran; at 20 ℃; for 16h;
DOI:10.1016/j.carres.2012.04.011

Reference yield:

: 141422-28-8,99605-28-4
3-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidyne-α-D-glucofuranose

: 1384188-40-2
3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-tert-butyldimethylsilyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-Bromosuccinimide; triphenylphosphine / N,N-dimethyl-formamide / 3.5 h / 20 °C / Cooling with ice; Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 2.5 h / Reflux

3.1: tetrahydrofuran / 2.5 h / 105 °C / Microwave irradiation

3.2: 16 h / 20 °C

With N-Bromosuccinimide; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.carres.2012.04.011

Reference yield:

: 99605-27-3
3-O-(tert-butyldimethylsilyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 1384188-40-2
3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-tert-butyldimethylsilyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole

Guidance literature:: Multi-step reaction with 4 steps

1.1: / 48 h

2.1: N-Bromosuccinimide; triphenylphosphine / N,N-dimethyl-formamide / 3.5 h / 20 °C / Cooling with ice; Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 2.5 h / Reflux

4.1: tetrahydrofuran / 2.5 h / 105 °C / Microwave irradiation

4.2: 16 h / 20 °C

With N-Bromosuccinimide; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.carres.2012.04.011