[1S,2R]-[3-(dimethylphenylsilanyl)-1-hydroxymethyl-2-methylbut-3-enyl]carbamic acid tert-butyl ester

Base Information

Chemical Name:[1S,2R]-[3-(dimethylphenylsilanyl)-1-hydroxymethyl-2-methylbut-3-enyl]carbamic acid tert-butyl ester
CAS No.:864360-69-0
Molecular Formula:C₁₉H₃₁NO₃Si
Molecular Weight:349.546
Hs Code.:

Synonyms:[1S,2R]-[3-(dimethylphenylsilanyl)-1-hydroxymethyl-2-methylbut-3-enyl]carbamic acid tert-butyl ester

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Chemical Property of [1S,2R]-[3-(dimethylphenylsilanyl)-1-hydroxymethyl-2-methylbut-3-enyl]carbamic acid tert-butyl ester

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Technology Process of [1S,2R]-[3-(dimethylphenylsilanyl)-1-hydroxymethyl-2-methylbut-3-enyl]carbamic acid tert-butyl ester

There total 6 articles about [1S,2R]-[3-(dimethylphenylsilanyl)-1-hydroxymethyl-2-methylbut-3-enyl]carbamic acid tert-butyl 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: 79.0%

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

: 864360-69-0
[1S,2R]-[3-(dimethylphenylsilanyl)-1-hydroxymethyl-2-methylbut-3-enyl]carbamic acid tert-butyl ester

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 1.5h;
DOI:10.1039/b506198a

Reference yield:

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

: 864360-69-0
[1S,2R]-[3-(dimethylphenylsilanyl)-1-hydroxymethyl-2-methylbut-3-enyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 79 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 °C

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

Reference yield:

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

: 864360-69-0
[1S,2R]-[3-(dimethylphenylsilanyl)-1-hydroxymethyl-2-methylbut-3-enyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 55 percent / KHMDS; DMPU / tetrahydrofuran; toluene / 2 h / 20 °C

2: 79 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium aluminium tetrahydride; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; toluene; 1: aza-<2,3>-Wittig sigmatropic rearrangement;
DOI:10.1039/b506198a