(2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine

Base Information

• Chemical Name: (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine
• CAS No.: 173251-23-5
• Molecular Formula: C₃₂H₄₈N₂O₅S₂
• Molecular Weight: 604.876
• Mol file: 173251-23-5.mol

Synonyms:(2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine

Chemical Property of (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine

There total 9 articles about (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine 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: 80.0%

methyl (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine (219913-99-2) → (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine (173251-23-5)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; for 1h; Ambient temperature;

DOI:10.1021/jo981892c

Reference yield:

(2R,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenal (173251-18-8) → (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine (173251-23-5)

Guidance literature:

Multi-step reaction with 6 steps

1: CrCl₂, Ni(COD)2 / tetrahydrofuran / Ambient temperature

2: 77 percent / Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

3: 1.) CuCN, 2.) BF₃*OEt₂ / 1.) THF, -20 deg C to room temperature, 2.) THF, -78 deg C, 20 min

4: aq. LiOH / dioxane / 23 h / Ambient temperature

5: 100 percent / NMM, HOBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 16 h / Ambient temperature

6: 80 percent / aq. LiOH / dioxane / 1 h / Ambient temperature

With 4-methyl-morpholine; chromium dichloride; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium hydroxide; boron trifluoride diethyl etherate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo981892c

Reference yield:

methyl (2R/S,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenoate → (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine (173251-23-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 68 percent / DIBAL / toluene; hexane / 0.25 h / Ambient temperature

2: 1.) (COCl)2, DMSO, 2.) TEA / 1.) CH₂Cl₂, -60 deg C, 10 min, 2.) -60 deg C to room temperature

3: CrCl₂, Ni(COD)2 / tetrahydrofuran / Ambient temperature

4: 77 percent / Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

5: 1.) CuCN, 2.) BF₃*OEt₂ / 1.) THF, -20 deg C to room temperature, 2.) THF, -78 deg C, 20 min

6: aq. LiOH / dioxane / 23 h / Ambient temperature

7: 100 percent / NMM, HOBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 16 h / Ambient temperature

8: 80 percent / aq. LiOH / dioxane / 1 h / Ambient temperature

With 4-methyl-morpholine; chromium dichloride; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium hydroxide; oxalyl dichloride; TEA; boron trifluoride diethyl etherate; diisobutylaluminium hydride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo981892c

upstream raw materials:

methyl (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine

(2R,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenal

(2R,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenol

methyl (2E,4R,5R,6E)-4-hydroxy-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoate

Downstream raw materials:

(2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine

(2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-amino-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine

Refernces