Benzyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate

Base Information

• Chemical Name: Benzyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate
• CAS No.: 69871-79-0
• Molecular Formula: C22H27NO5
• Molecular Weight: 385.46
• DSSTox Substance ID: DTXSID20538996
• Nikkaji Number: J1.053.562J
• Wikidata: Q82414590
• Mol file: 69871-79-0.mol

Synonyms:69871-79-0;BocSer(Bzl)OBzl;SCHEMBL7518373;DTXSID20538996;GPPPVJZIRFVEMC-IBGZPJMESA-N;Benzyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate

Chemical Property of Benzyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 385.18892296
• Heavy Atom Count: 28
• Complexity: 476

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(COCC1=CC=CC=C1)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](COCC1=CC=CC=C1)C(=O)OCC2=CC=CC=C2

Technology Process of Benzyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate

There total 6 articles about Benzyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate 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: 100.0%

BOC-O-benzyl-L-serine (23680-31-1) + benzyl bromide (100-39-0) → (S)-benzyl 3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoate (69871-79-0)

Guidance literature:

BOC-O-benzyl-L-serine; With caesium carbonate; In methanol;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1039/b001612h

Reference yield: 89.0%

N,N-dimethylformamide dibenzyl acetal (2016-04-8) + BOC-O-benzyl-L-serine (23680-31-1) → (S)-benzyl 3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoate (69871-79-0)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 15h;

DOI:10.1016/S0040-4020(98)00882-5

Reference yield:

BOC-O-benzyl-L-serine (23680-31-1) + benzyl alcohol (100-51-6,185532-71-2) → (S)-benzyl 3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoate (69871-79-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo051004v

upstream raw materials:

BOC-O-benzyl-L-serine

benzyl bromide

N,N-dimethylformamide dibenzyl acetal

benzyl alcohol

Downstream raw materials:

Ser(Bzl)-OBzl

(S)-2-((S)-2-Amino-3-benzyloxy-propionylamino)-3-benzyloxy-propionic acid benzyl ester

Boc-Leu-Ser(Bzl)-OBzl

Boc-Ser(Bzl)-Ser(Bzl)-OBzl