(R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide

Base Information

• Chemical Name: (R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide
• CAS No.: 321435-46-5
• Molecular Formula: C₃₉H₅₄N₄O₇SSi
• Molecular Weight: 751.032
• Mol file: 321435-46-5.mol

Synonyms:(R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide

Chemical Property of (R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide

There total 12 articles about (R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide 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:

cis-4-amino-3-chromanol (138603-50-6) + (2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-{(R)-4-[(3,5-dimethyl-isoxazol-4-ylmethyl)-carbamoyl]-5,5-dimethyl-thiazolidin-3-yl}-5-oxo-pentanoic acid → (R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide (321435-46-5)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0960-894X(03)00262-2

Reference yield:

dihydro-5(S)-(hydroxymethyl)-3(R)-(phenylmethyl)-3(2H)-furanone (150407-67-3) → (R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide (321435-46-5)

Guidance literature:

Multi-step reaction with 8 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

8: HBTU; DIEA; HOAT / dimethylformamide / 20 °C

With morpholine; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; jones' reagent; water; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0960-894X(03)00262-2

Reference yield:

(R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (117918-23-7) → (R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide (321435-46-5)

Guidance literature:

Multi-step reaction with 9 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

9: HBTU; DIEA; HOAT / dimethylformamide / 20 °C

With morpholine; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; water; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 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

upstream raw materials:

cis-4-amino-3-chromanol

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

(R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

(R)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid