[2S,3R]-2-N-tert-butoxycarbonyl-amino-4-(dimethylphenylsilanyl)-3-menthylpent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

Base Information

Chemical Name:[2S,3R]-2-N-tert-butoxycarbonyl-amino-4-(dimethylphenylsilanyl)-3-menthylpent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester
CAS No.:864360-67-8
Molecular Formula:C₃₅H₅₁NO₄Si
Molecular Weight:577.88
Hs Code.:

Synonyms:[2S,3R]-2-N-tert-butoxycarbonyl-amino-4-(dimethylphenylsilanyl)-3-menthylpent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

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Chemical Property of [2S,3R]-2-N-tert-butoxycarbonyl-amino-4-(dimethylphenylsilanyl)-3-menthylpent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

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Technology Process of [2S,3R]-2-N-tert-butoxycarbonyl-amino-4-(dimethylphenylsilanyl)-3-menthylpent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

There total 5 articles about [2S,3R]-2-N-tert-butoxycarbonyl-amino-4-(dimethylphenylsilanyl)-3-menthylpent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester 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: 55.0%

: 864360-66-7
N-tert-butoxycarbonyl-N-[2-(dimethylphenylsilanyl)but-2(Z)-enyl]glycine-(1R,2S,5R)-8-phenylmenthol ester

: [2R,3S]-2-N-tert-butoxycarbonyl-amino-4-(dimethylphenylsilanyl)-3-menthylpent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

: 864360-67-8
[2S,3R]-2-N-tert-butoxycarbonyl-amino-4-(dimethylphenylsilanyl)-3-menthylpent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

Guidance literature:: With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 20 ℃; for 2h;
DOI:10.1039/b506198a

Reference yield:

: 31954-27-5
N-(tert-butoxycarbonyl)glycine methyl ester

: 864360-67-8
[2S,3R]-2-N-tert-butoxycarbonyl-amino-4-(dimethylphenylsilanyl)-3-menthylpent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / KH / tetrahydrofuran / 0 - 20 °C

2: 97 percent / aq. NaOH / tetrahydrofuran / 21 h / 20 °C

3: 93 percent / DCC; DMAP / CH₂Cl₂ / 14 h / -30 - 20 °C

4: 55 percent / KHMDS; DMPU / tetrahydrofuran; toluene / 2 h / 20 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydroxide; potassium hydride; potassium hexamethylsilazane; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene; 4: aza-<2,3>-Wittig sigmatropic rearrangement;
DOI:10.1039/b506198a

Reference yield:

: 320618-66-4
1-bromo-2-(dimethylphenylsilanyl)but-2(E)-ene

: 864360-67-8
[2S,3R]-2-N-tert-butoxycarbonyl-amino-4-(dimethylphenylsilanyl)-3-menthylpent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / KH / tetrahydrofuran / 0 - 20 °C

2: 97 percent / aq. NaOH / tetrahydrofuran / 21 h / 20 °C

3: 93 percent / DCC; DMAP / CH₂Cl₂ / 14 h / -30 - 20 °C

4: 55 percent / KHMDS; DMPU / tetrahydrofuran; toluene / 2 h / 20 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydroxide; potassium hydride; potassium hexamethylsilazane; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene; 4: aza-<2,3>-Wittig sigmatropic rearrangement;
DOI:10.1039/b506198a