5-acetoxy-3(S)-(tert-butyldimethylsilanyloxy)-4(R)-(1'(S)-α-methylbenzylamino)-pentanoic acid tert-butyl ester

Base Information

Chemical Name:5-acetoxy-3(S)-(tert-butyldimethylsilanyloxy)-4(R)-(1'(S)-α-methylbenzylamino)-pentanoic acid tert-butyl ester
CAS No.:312728-22-6
Molecular Formula:C₂₅H₄₃NO₅Si
Molecular Weight:465.706
Hs Code.:

Synonyms:5-acetoxy-3(S)-(tert-butyldimethylsilanyloxy)-4(R)-(1'(S)-α-methylbenzylamino)-pentanoic acid tert-butyl ester

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Chemical Property of 5-acetoxy-3(S)-(tert-butyldimethylsilanyloxy)-4(R)-(1'(S)-α-methylbenzylamino)-pentanoic acid tert-butyl ester

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Technology Process of 5-acetoxy-3(S)-(tert-butyldimethylsilanyloxy)-4(R)-(1'(S)-α-methylbenzylamino)-pentanoic acid tert-butyl ester

There total 5 articles about 5-acetoxy-3(S)-(tert-butyldimethylsilanyloxy)-4(R)-(1'(S)-α-methylbenzylamino)-pentanoic 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: 94.0%

: 64-19-7,77671-22-8
acetic acid

: 312728-21-5
3(S)-(tert-butyldimethylsilanyloxy)-3-[1-(1'(S)-α-methylbenzyl)-aziridin-2(R)-yl]-propionic acid tert-butyl ester

: 312728-22-6
5-acetoxy-3(S)-(tert-butyldimethylsilanyloxy)-4(R)-(1'(S)-α-methylbenzylamino)-pentanoic acid tert-butyl ester

Guidance literature:: In dichloromethane; at 20 ℃; for 10h;
DOI:10.1016/S0957-4166(00)00311-6

Reference yield:

: 540-88-5
acetic acid tert-butyl ester

: 312728-22-6
5-acetoxy-3(S)-(tert-butyldimethylsilanyloxy)-4(R)-(1'(S)-α-methylbenzylamino)-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 88 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: 8 percent / NaBH₄ / propan-2-ol / 1 h / -40 °C

3.1: 90 percent / DMAP; TEA / CH₂Cl₂ / 17 h / 20 °C

4.1: 94 percent / CH₂Cl₂ / 10 h / 20 °C

With dmap; sodium tetrahydroborate; TEA; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; isopropyl alcohol; 1.1: Metallation / 1.2: Condensation / 2.1: Reduction / 3.1: silylation / 4.1: Ring cleavage;
DOI:10.1016/S0957-4166(00)00311-6

Reference yield:

: 68820-71-3
ethyl 1-[(S)-1-phenylethyl]aziridine-(R)-carboxylate

: 312728-22-6
5-acetoxy-3(S)-(tert-butyldimethylsilanyloxy)-4(R)-(1'(S)-α-methylbenzylamino)-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 88 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: 8 percent / NaBH₄ / propan-2-ol / 1 h / -40 °C

3.1: 90 percent / DMAP; TEA / CH₂Cl₂ / 17 h / 20 °C

4.1: 94 percent / CH₂Cl₂ / 10 h / 20 °C

With dmap; sodium tetrahydroborate; TEA; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; isopropyl alcohol; 1.1: Metallation / 1.2: Condensation / 2.1: Reduction / 3.1: silylation / 4.1: Ring cleavage;
DOI:10.1016/S0957-4166(00)00311-6