C₆H₅CH₂CH₂CO-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH₃

Base Information

• Chemical Name: C₆H₅CH₂CH₂CO-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH₃
• CAS No.: 158395-16-5
• Molecular Formula: C₅₄H₆₅N₅O₆S₃
• Molecular Weight: 976.338
• Mol file: 158395-16-5.mol

Synonyms:C₆H₅CH₂CH₂CO-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH₃

Chemical Property of C₆H₅CH₂CH₂CO-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₆H₅CH₂CH₂CO-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH₃

There total 19 articles about C₆H₅CH₂CH₂CO-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH₃ 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: 88.0%

hydrocinnamic acid chloride (645-45-4) + (2S,3R)-2-{(R)-2-[(R)-2-((R)-2-Amino-3-benzylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-2-methyl-propionylamino]-3-benzylsulfanyl-2-methyl-propionylamino}-3-benzyloxy-N-methyl-butyramide → C6H5CH2CH2CO-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH3 (158395-16-5)

Guidance literature:

With triethylamine; In chloroform; at 25 ℃;

DOI:10.1016/S0040-4020(99)00604-3

Reference yield: 85.0%

O-benzylthreonine N-methylamide hydrochloride + (R)-3-Benzylsulfanyl-2-{(R)-3-benzylsulfanyl-2-[(R)-3-benzylsulfanyl-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-2-methyl-propionic acid (158395-14-3) → C6H5CH2CH2CO-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH3 (158395-16-5)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00096a012

Reference yield:

Boc-L-Thr(Bn)-NHCH3 (149639-95-2) → C6H5CH2CH2CO-(R)-MeCys(Bn)-(R)-MeCys(Bn)-(R)-MeCys(Bn)-Thr(Bn)-NHCH3 (158395-16-5)

Guidance literature:

Multi-step reaction with 8 steps

1: TFA; anisole

2: 77 percent / CIP; DIEA; HOAt / tetrahydrofuran / 12 h / 25 °C

3: TFA; anisole

4: 72 percent / CIP; DIEA; HOAt / tetrahydrofuran / 72 h / 25 °C

5: TFA; anisole

6: 42 percent / CIP; DIEA; HOAt / tetrahydrofuran / 48 h / 25 °C

7: TFA; anisole

8: 88 percent / Et₃N / CHCl₃ / 25 °C

With 1-hydroxy-7-aza-benzotriazole; methoxybenzene; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; chloroform; 1: Hydrolysis / 2: Condensation / 3: Hydrolysis / 4: Condensation / 5: Hydrolysis / 6: Condensation / 7: Hydrolysis / 8: Acylation;

DOI:10.1016/S0040-4020(99)00604-3

upstream raw materials:

(R)-3-Benzylsulfanyl-2-{(R)-3-benzylsulfanyl-2-[(R)-3-benzylsulfanyl-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-2-methyl-propionic acid

hydrocinnamic acid chloride

N-Boc-O-benzyl-L-threonine

N^α-benzyloxycarbonyl-S-benzyl-(R)-methylcysteine

Downstream raw materials:

(2S,3R)-3-Hydroxy-2-((R)-3-mercapto-2-{(R)-3-mercapto-2-[(R)-3-mercapto-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-2-methyl-propionylamino)-N-methyl-butyramide