(4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl ester

Base Information

Chemical Name:(4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl ester
CAS No.:873914-62-6
Molecular Formula:C₂₄H₃₉NO₅Si
Molecular Weight:449.663
Hs Code.:

Synonyms:(4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl ester

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Chemical Property of (4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl ester

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Technology Process of (4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl ester

There total 9 articles about (4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl 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: 91.0%

: (2R,3S)-2-tert-butyldimethylsilyloxy-3-tert-butoxycarbonyl-amino-3-phenylpropanal

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 873914-62-6
(4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl ester

Guidance literature:: In tetrahydrofuran; at 25 ℃; for 24h;
DOI:10.1016/j.tetasy.2005.09.010

Reference yield:

: 873914-61-5
(2R,3S)-2-[(tert-butyldimethyl-silanyloxy)-3-hydroxy-1-phenylpropyl]-carbamic acid tert-butyl ester

: 873914-62-6
(4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: PCC; Celite; CH₃CO₂Na / CH₂Cl₂ / 5 h / 25 °C

2: 91 percent / tetrahydrofuran / 24 h / 25 °C

With Celite; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 2: Wittig reaction;
DOI:10.1016/j.tetasy.2005.09.010

Reference yield:

: 60512-85-8
(E)-isopropyl cinnamate

: 873914-62-6
(4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)-5-phenylpent-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 76 percent / K₂[OsO₂(OH)4]; LiOH*H₂O; (DHQ)2PHAL / H₂O; 2-methyl-propan-2-ol / 4 h / 4 °C

2: aq. HCl / 15 h / Heating

3: 0.54 g / Et₃N / CH₂Cl₂ / 24.5 h / 0 - 25 °C

4: 91 percent / imidazole; DMAP / CH₂Cl₂ / 10 h / 25 °C

5: 93 percent / DIBAL-H / CH₂Cl₂ / 3 h / 0 - 25 °C

6: PCC; Celite; CH₃CO₂Na / CH₂Cl₂ / 5 h / 25 °C

7: 91 percent / tetrahydrofuran / 24 h / 25 °C

With 1H-imidazole; hydrogenchloride; dmap; lithium hydroxide; Hydroquinone 1,4-phthalazinediyl diether; K2; Celite; sodium acetate; diisobutylaluminium hydride; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1: Sharpless asymmetric aminohydroxylation / 7: Wittig reaction;
DOI:10.1016/j.tetasy.2005.09.010