(2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-{(R)-5,5-dimethyl-4-[(3-methyl-pyridin-2-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-5-oxo-pentanoic acid

Base Information

Chemical Name:(2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-{(R)-5,5-dimethyl-4-[(3-methyl-pyridin-2-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-5-oxo-pentanoic acid
CAS No.:321435-44-3
Molecular Formula:C₃₁H₄₅N₃O₅SSi
Molecular Weight:599.867
Hs Code.:

(2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-{(R)-5,5-dimethyl-4-[(3-methyl-pyridin-2-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-5-oxo-pentanoic acid

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Chemical Property of (2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-{(R)-5,5-dimethyl-4-[(3-methyl-pyridin-2-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-5-oxo-pentanoic acid

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Technology Process of (2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-{(R)-5,5-dimethyl-4-[(3-methyl-pyridin-2-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-5-oxo-pentanoic acid

There total 11 articles about (2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-{(R)-5,5-dimethyl-4-[(3-methyl-pyridin-2-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-5-oxo-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:

: C₃₇H₅₉N₃O₅SSi₂

: 321435-44-3
(2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-{(R)-5,5-dimethyl-4-[(3-methyl-pyridin-2-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-5-oxo-pentanoic acid

Guidance literature:: With water; In tetrahydrofuran;
DOI:10.1016/S0960-894X(03)00262-2

Reference yield:

: 150407-67-3
dihydro-5(S)-(hydroxymethyl)-3(R)-(phenylmethyl)-3(2H)-furanone

: 321435-44-3
(2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-{(R)-5,5-dimethyl-4-[(3-methyl-pyridin-2-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-5-oxo-pentanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: Jones' reagent / acetone

2: 47 percent / Py*Brop; HOAT; DIEA / CH₂Cl₂ / 20 °C

3: 85 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 20 °C

4: EDC; HOAT; DIEA / CH₂Cl₂ / 20 °C

5: aq. LiOH / dioxane / 20 °C

6: DIEA / CH₂Cl₂ / 20 °C

7: H₂O / tetrahydrofuran

With morpholine; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; jones' reagent; water; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetone;
DOI:10.1016/S0960-894X(03)00262-2

Reference yield:

: 117918-23-7
(R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

: 321435-44-3
(2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-{(R)-5,5-dimethyl-4-[(3-methyl-pyridin-2-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-5-oxo-pentanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 80 percent / Et₃N / dimethylformamide / 20 °C

2: 100 percent / TFA / CH₂Cl₂

3: 47 percent / Py*Brop; HOAT; DIEA / CH₂Cl₂ / 20 °C

4: 85 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 20 °C

5: EDC; HOAT; DIEA / CH₂Cl₂ / 20 °C

6: aq. LiOH / dioxane / 20 °C

7: DIEA / CH₂Cl₂ / 20 °C

8: H₂O / tetrahydrofuran

With morpholine; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; water; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(03)00262-2