13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

Base Information

Chemical Name:13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin
CAS No.:174729-14-7
Molecular Formula:C₄₄H₄₅BrCl₆O₁₆
Molecular Weight:1122.45
Hs Code.:

Synonyms:13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

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Chemical Property of 13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

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Technology Process of 13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

There total 4 articles about 13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin 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: 96.0%

: 13-O-((3R)-3-phenylglycidoyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

: 13-O-((2R,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

: 174729-14-7
13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

Guidance literature:: 13-O-((3R)-3-phenylglycidoyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin; With magnesium dibromide etherate; In diethyl ether; at -18 - 3 ℃; for 120h;

With water; sodium chloride; In diethyl ether; Reagent/catalyst; Solvent; Temperature; regioselective reaction;
DOI:10.1007/s11172-012-0302-4

Reference yield: 76.0%

: 174847-58-6
C₄₄H₄₄Cl₆O₁₆

: 174729-14-7
13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; titanium(IV) bromide; In dichloromethane; at 0 ℃; for 18h;
DOI:10.1016/S0040-4020(98)01108-9

Reference yield:

: 115794-67-7
methyl (2R,3S)-3-phenylglycidate

: 174729-14-7
13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

Guidance literature:: Multi-step reaction with 3 steps

1: NaOH / tetrahydrofuran; H₂O / 0.33 h / Ambient temperature

2: 5.55 g / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 0.17 h / Ambient temperature

3: 76 percent / hexamethylphosphoramide, TiBr₄ / CH₂Cl₂ / 18 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; titanium(IV) bromide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1016/S0040-4020(98)01108-9