(2R,3R,4S)-2-benzyl-4-((2S)-2-tert-butoxycarbonylamino-3-hydroxypropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid

Base Information

Chemical Name:(2R,3R,4S)-2-benzyl-4-((2S)-2-tert-butoxycarbonylamino-3-hydroxypropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid
CAS No.:210300-12-2
Molecular Formula:C₂₆H₄₃NO₈Si
Molecular Weight:525.715
Hs Code.:

Synonyms:(2R,3R,4S)-2-benzyl-4-((2S)-2-tert-butoxycarbonylamino-3-hydroxypropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid

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Chemical Property of (2R,3R,4S)-2-benzyl-4-((2S)-2-tert-butoxycarbonylamino-3-hydroxypropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid

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Technology Process of (2R,3R,4S)-2-benzyl-4-((2S)-2-tert-butoxycarbonylamino-3-hydroxypropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid

There total 10 articles about (2R,3R,4S)-2-benzyl-4-((2S)-2-tert-butoxycarbonylamino-3-hydroxypropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid 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: 100.0%

: 215798-03-1
(2R,3R,4S)-2-benzyl-4-((2S)-3-benzyloxy-2-tert-butoxycarbonylaminopropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid benzyl ester

: 210300-12-2
(2R,3R,4S)-2-benzyl-4-((2S)-2-tert-butoxycarbonylamino-3-hydroxypropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid

Guidance literature:: With hydrogen; palladium dihydroxide; In ethanol; at 25 ℃; for 14h; under 3040 Torr;
DOI:10.1016/S0040-4020(98)00777-7

Reference yield:

: 210300-08-6
(2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid benzyl ester

: 210300-12-2
(2R,3R,4S)-2-benzyl-4-((2S)-2-tert-butoxycarbonylamino-3-hydroxypropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: DMAP, EDCI / CH₂Cl₂ / 2 h / 10 °C

2: 100 percent / H₂ / Pd(OH)2 / ethanol / 14 h / 25 °C / 3040 Torr

With dmap; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium dihydroxide; In ethanol; dichloromethane;
DOI:10.1016/S0040-4020(98)00777-7

Reference yield:

: 96837-44-4
(R)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one

: 210300-12-2
(2R,3R,4S)-2-benzyl-4-((2S)-2-tert-butoxycarbonylamino-3-hydroxypropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid

Guidance literature:: Multi-step reaction with 7 steps

2: aq. H₂O₂, LiOH / 12 h / 25 °C

3: 89 percent / triphenylphosphine, DIAD / tetrahydrofuran / 0.67 h / 25 °C

4: 99 percent / imidazole / dimethylformamide / 17 h / 60 °C

5: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 0.5 h / 25 °C

6: DMAP, EDCI / CH₂Cl₂ / 2 h / 10 °C

7: 100 percent / H₂ / Pd(OH)2 / ethanol / 14 h / 25 °C / 3040 Torr

With 1H-imidazole; dmap; lithium hydroxide; di-isopropyl azodicarboxylate; hydrogen; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00777-7