2-(2-Bromo-5-dimethylamino-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide

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Chemical Name:2-(2-Bromo-5-dimethylamino-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide
CAS No.:163913-96-0
Molecular Formula:C₃₇H₆₇BrN₂O₇Si₃
Molecular Weight:816.109
Hs Code.:

2-(2-Bromo-5-dimethylamino-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide

Synonyms:2-(2-Bromo-5-dimethylamino-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide

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Chemical Property of 2-(2-Bromo-5-dimethylamino-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide

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Technology Process of 2-(2-Bromo-5-dimethylamino-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide

There total 7 articles about 2-(2-Bromo-5-dimethylamino-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide 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: 42.0%

: 163914-14-5
1-bromo-2-(bromomethyl)-4-(dimethylamino)benzene

: 136380-26-2
N-methoxy-N-methyl-6,7,13-O-tris(trimethylsilyl)monoamide

: 163913-96-0
2-(2-Bromo-5-dimethylamino-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide

Guidance literature:: With tert.-butyl lithium; diisopropylamine; dmap; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)73095-4

Reference yield:

: 99-64-9
3-(dimethylamino)benzoic acid

: 163913-96-0
2-(2-Bromo-5-dimethylamino-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / conc. H₂SO₄ / 16 h / Heating

2: 91 percent / 2,4,4,6-tetrabromocyclohexadienone / CH₂Cl₂ / -20 deg C, 1 h; to RT, 2 h

3: 78 percent / diisobutylaluminium hydride / tetrahydrofuran / 2 h / -70 °C

4: 75 percent / PPh₃, bromine / CH₂Cl₂ / 1 h / -20 °C

5: 42 percent / 10 mol percent i-Pr₂NH, t-BuLi / 10 mol percent 4-dimethylaminopyridine / tetrahydrofuran

With sulfuric acid; 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; bromine; tert.-butyl lithium; diisobutylaluminium hydride; diisopropylamine; triphenylphosphine; dmap; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(00)73095-4

Reference yield:

: 16518-64-2
3-(dimethylamino)benzoic acid methyl ester

: 163913-96-0
2-(2-Bromo-5-dimethylamino-benzyl)-3-{(2S,3S,4R,5S)-5-[(2S,3S)-3-((1R,2S)-1-methyl-2-trimethylsilanyloxy-propyl)-oxiranylmethyl]-3,4-bis-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / 2,4,4,6-tetrabromocyclohexadienone / CH₂Cl₂ / -20 deg C, 1 h; to RT, 2 h

2: 78 percent / diisobutylaluminium hydride / tetrahydrofuran / 2 h / -70 °C

3: 75 percent / PPh₃, bromine / CH₂Cl₂ / 1 h / -20 °C

4: 42 percent / 10 mol percent i-Pr₂NH, t-BuLi / 10 mol percent 4-dimethylaminopyridine / tetrahydrofuran

With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; bromine; tert.-butyl lithium; diisobutylaluminium hydride; diisopropylamine; triphenylphosphine; dmap; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(00)73095-4