(2S,3R)-3-[(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Base Information

Chemical Name:(2S,3R)-3-[(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester
CAS No.:178113-64-9
Molecular Formula:C₄₁H₆₉NO₉Si
Molecular Weight:748.086
Hs Code.:

(2S,3R)-3-[(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Synonyms:(2S,3R)-3-[(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

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Chemical Property of (2S,3R)-3-[(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

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Technology Process of (2S,3R)-3-[(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

There total 10 articles about (2S,3R)-3-[(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl 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: 97.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: (2S,3R)-3-((3R,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

: 178113-64-9
(2S,3R)-3-[(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 20h; Ambient temperature;
DOI:10.1016/0040-4020(96)00951-9

Reference yield:

: 124-13-0
Octanal

: 178113-64-9
(2S,3R)-3-[(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, a) -78 deg C, 30 min, b) RT, 2 h

2: 71 percent / n-BuOLi / tetrahydrofuran / 1 h / 0 °C

3: DCC, DMAP / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) RT, 40 h

4: H₂ / Pd(OH)2 / ethanol / 2 h / Ambient temperature

5: DCC, DMAP / CH₂Cl₂ / 14 h / 0 - 20 °C

6: 24 percent / TsOH / methanol / 72 h / Ambient temperature

7: 97 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

With 1H-imidazole; dmap; di-n-butylboryl trifluoromethanesulfonate; hydrogen; lithium butoxide; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(96)00951-9

Reference yield:

: 178113-53-6
(4S,5R)-3-((2S,3R)-3-hydroxy-2-methyl-1-oxodecanyl)-4-methyl-5-phenyl-2-oxazolidinone

: 178113-64-9
(2S,3R)-3-[(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 71 percent / n-BuOLi / tetrahydrofuran / 1 h / 0 °C

2: DCC, DMAP / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) RT, 40 h

3: H₂ / Pd(OH)2 / ethanol / 2 h / Ambient temperature

4: DCC, DMAP / CH₂Cl₂ / 14 h / 0 - 20 °C

5: 24 percent / TsOH / methanol / 72 h / Ambient temperature

6: 97 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

With 1H-imidazole; dmap; hydrogen; lithium butoxide; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(96)00951-9