S-benzyl-N-[N²-(N²-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester

Base Information

• Chemical Name: S-benzyl-N-[N²-(N²-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester
• CAS No.: 2658-34-6
• Molecular Formula: C₂₈H₃₅N₅O₈S
• Molecular Weight: 601.681
• Mol file: 2658-34-6.mol

Synonyms:S-benzyl-N-[N²-(N²-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester

Chemical Property of S-benzyl-N-[N²-(N²-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-benzyl-N-[N²-(N²-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester

There total 4 articles about S-benzyl-N-[N²-(N²-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine 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:

Cbz-L-Gln (2650-64-8) + N-L-asparaginyl-S-benzyl-L-cysteine methyl ester (86961-92-4) → 1,4-dioxane (123-91-1,28347-88-8,28347-91-3,39449-24-6,54841-74-6) + S-benzyl-N-[N2-(N2-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester (2658-34-6)

Guidance literature:

With tetrahydrofuran; chloroformic acid ethyl ester; triethylamine; Reagens 4: H₂O;

DOI:10.1002/hlca.19550380622

Reference yield:

S-benzylcysteine methyl ester (22728-88-7) → S-benzyl-N-[N2-(N2-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester (2658-34-6)

Guidance literature:

Multi-step reaction with 3 steps

1: isovaleryl chloride; triethylamine; THF / Reagens 4: THF;

2: HBr; acetic acid

3: dicyclohexylcarbodiimide; THF

With tetrahydrofuran; hydrogen bromide; acetic acid; triethylamine; dicyclohexyl-carbodiimide; isopentanoyl chloride;

DOI:10.1021/ja01543a051

Reference yield:

S-benzyl-N-(N2-benzyloxycarbonyl-L-asparaginyl)-L-cysteine methyl ester (20987-51-3) → S-benzyl-N-[N2-(N2-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester (2658-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr; acetic acid

2: dicyclohexylcarbodiimide; THF

With tetrahydrofuran; hydrogen bromide; acetic acid; dicyclohexyl-carbodiimide;

DOI:10.1021/ja01543a051

upstream raw materials:

Cbz-L-Gln

N-L-asparaginyl-S-benzyl-L-cysteine methyl ester

S-benzyl-N-(N²-benzyloxycarbonyl-L-asparaginyl)-L-cysteine methyl ester

S-benzylcysteine methyl ester

Downstream raw materials:

S-benzyl-N-[N²-(N²-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine

S-benzyl-N-[N²-(N²-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteinyl azide

N²-benzyloxycarbonyl-glutaminyl=>asparaginyl=>S-benzyl-cysteinyl=>prolyl=>leucyl=>-glycin-amide