N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-allylglycine methyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-allylglycine methyl ester
• CAS No.: 919487-72-2
• Molecular Formula: C₃₇H₃₈N₂O₅S
• Molecular Weight: 622.785
• Mol file: 919487-72-2.mol

Synonyms:N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-allylglycine methyl ester

Chemical Property of N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-allylglycine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-allylglycine methyl ester

There total 1 articles about N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-allylglycine methyl ester 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: 82.0%

2-benzyloxycarbonylamino-4-tritylsulfanyl-butyric acid + (S)-allylglycine methyl ester hydrochloride (173723-62-1,217440-34-1) → N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-allylglycine methyl ester (919487-72-2)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; cooling;

DOI:10.1021/jo061692y

Reference yield: 93.0%

N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-allylglycine methyl ester (919487-72-2) + carbon monoxide (201230-82-2) → N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-6-oxonorleucine methyl ester (919487-85-7)

Guidance literature:

With hydrogen; 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); acetylacetonatodicarbonylrhodium(l); In methanol; at 65 ℃; for 20h; under 3040 Torr;

DOI:10.1021/jo061692y

Reference yield:

N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-allylglycine methyl ester (919487-72-2) → (3S,7S,11S)-1-aza-3-benzyloxycarbonylamino-11-methoxycarbonyl-2-oxo-6-thiabicyclo[5.4.0]undecane (167305-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / hydrogen; BIPHEPHOS / Rh(acac)(CO)2 / methanol / 20 h / 65 °C / 3040 Torr

2.1: methanesulfonic acid / benzene / 20 °C

2.2: 90 percent / trifluoroacetic acid; Et₃SiH / benzene / cooling

With methanesulfonic acid; hydrogen; 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); acetylacetonatodicarbonylrhodium(l); In methanol; benzene;

DOI:10.1021/jo061692y

upstream raw materials:

(S)-allylglycine methyl ester hydrochloride

Downstream raw materials:

N-benzyloxycarbonyl-S-trityl-(S)-homocysteinyl-(S)-6-oxonorleucine methyl ester

(3S,7S,11S)-1-aza-3-benzyloxycarbonylamino-11-methoxycarbonyl-2-oxo-6-thiabicyclo[5.4.0]undecane