[3R,7S,7(1R),8S,9R]-8-bromo-7-(2-tert-butyldimethylsilyloxy-1-methylethyl)-3-phenyl-tetrahydrooxazolo[3,2-c][1,3]oxazin-5-one

Base Information

Chemical Name:[3R,7S,7(1R),8S,9R]-8-bromo-7-(2-tert-butyldimethylsilyloxy-1-methylethyl)-3-phenyl-tetrahydrooxazolo[3,2-c][1,3]oxazin-5-one
CAS No.:263722-28-7
Molecular Formula:C₂₁H₃₂BrNO₄Si
Molecular Weight:470.479
Hs Code.:

Synonyms:[3R,7S,7(1R),8S,9R]-8-bromo-7-(2-tert-butyldimethylsilyloxy-1-methylethyl)-3-phenyl-tetrahydrooxazolo[3,2-c][1,3]oxazin-5-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of [3R,7S,7(1R),8S,9R]-8-bromo-7-(2-tert-butyldimethylsilyloxy-1-methylethyl)-3-phenyl-tetrahydrooxazolo[3,2-c][1,3]oxazin-5-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of [3R,7S,7(1R),8S,9R]-8-bromo-7-(2-tert-butyldimethylsilyloxy-1-methylethyl)-3-phenyl-tetrahydrooxazolo[3,2-c][1,3]oxazin-5-one

There total 8 articles about [3R,7S,7(1R),8S,9R]-8-bromo-7-(2-tert-butyldimethylsilyloxy-1-methylethyl)-3-phenyl-tetrahydrooxazolo[3,2-c][1,3]oxazin-5-one 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: 93.0%

: 234123-03-6
[2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-oxazolidine

: 263722-28-7
[3R,7S,7(1R),8S,9R]-8-bromo-7-(2-tert-butyldimethylsilyloxy-1-methylethyl)-3-phenyl-tetrahydrooxazolo[3,2-c][1,3]oxazin-5-one

Guidance literature:: With N-Bromosuccinimide; In 1,2-dimethoxyethane; water; for 0.75h;
DOI:10.1016/S0040-4020(99)00949-7

Reference yield:

: 164530-43-2
Weinreb amide

: 263722-28-7
[3R,7S,7(1R),8S,9R]-8-bromo-7-(2-tert-butyldimethylsilyloxy-1-methylethyl)-3-phenyl-tetrahydrooxazolo[3,2-c][1,3]oxazin-5-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 77 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - -10 °C

2.1: 95 percent / Zn(BH₄)2 / diethyl ether / 1 h / 0 °C

3.1: 85 percent / Red-Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

4.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

5.1: copper iodide / tetrahydrofuran; diethyl ether / -78 - -20 °C

5.2: tetrahydrofuran; diethyl ether / 1 h / -60 °C

6.1: 93 percent / NBS / 1,2-dimethoxy-ethane; H₂O / 0.75 h

With N-Bromosuccinimide; copper(l) iodide; n-butyllithium; zinc(II) tetrahydroborate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; toluene; 1.1: Substitution / 2.1: Reduction / 3.1: Reduction / 4.1: mesylation / 5.1: Addition / 5.2: Methylation / 6.1: Cyclization;
DOI:10.1016/S0040-4020(99)00949-7

Reference yield:

: 179600-33-0
[2R,2(1S),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-hydroxy-but-2-ynyl)-4-phenyl-1,3-oxazolidine

: 263722-28-7
[3R,7S,7(1R),8S,9R]-8-bromo-7-(2-tert-butyldimethylsilyloxy-1-methylethyl)-3-phenyl-tetrahydrooxazolo[3,2-c][1,3]oxazin-5-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / Red-Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

2.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

3.1: copper iodide / tetrahydrofuran; diethyl ether / -78 - -20 °C

3.2: tetrahydrofuran; diethyl ether / 1 h / -60 °C

4.1: 93 percent / NBS / 1,2-dimethoxy-ethane; H₂O / 0.75 h

With N-Bromosuccinimide; copper(l) iodide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; toluene; 1.1: Reduction / 2.1: mesylation / 3.1: Addition / 3.2: Methylation / 4.1: Cyclization;
DOI:10.1016/S0040-4020(99)00949-7