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

Base Information

• Chemical Name: (2R,3E,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine
• CAS No.: 219914-10-0
• Molecular Formula: C₃₁H₄₆N₂O₇S₃
• Molecular Weight: 654.913
• Mol file: 219914-10-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2R,3E,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl 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: 92.0%

metgoxycarbonylsulfenyl chloride (26555-40-8) + (2R,3E,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine (219914-08-6) → (2R,3E,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine (219914-10-0)

Guidance literature:

With sodium acetate; In water; acetic acid; N,N-dimethyl-formamide; for 0.25h;

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) → (2R,3E,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine (219914-10-0)

Guidance literature:

Multi-step reaction with 7 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: 33 percent / aq. LiOH / dioxane / 23 h / Ambient temperature

5: 68 percent / NMM, HOBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 16 h / Ambient temperature

6: 86 percent / aq. LiOH / dioxane / 1 h / Ambient temperature

7: 92 percent / NaOAc*H₂O / acetic acid; H₂O; dimethylformamide / 0.25 h

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

DOI:10.1021/jo981892c

Reference yield:

(2R,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenol (173251-17-7) → (2R,3E,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine (219914-10-0)

Guidance literature:

Multi-step reaction with 8 steps

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

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

3: 77 percent / Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

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

5: 33 percent / aq. LiOH / dioxane / 23 h / Ambient temperature

6: 68 percent / NMM, HOBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 16 h / Ambient temperature

7: 86 percent / aq. LiOH / dioxane / 1 h / Ambient temperature

8: 92 percent / NaOAc*H₂O / acetic acid; H₂O; dimethylformamide / 0.25 h

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

DOI:10.1021/jo981892c

upstream raw materials:

metgoxycarbonylsulfenyl chloride

(2R,3E,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

Downstream raw materials:

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

Refernces