Boc-Asp(OBzl)-OSu

Base Information

• Chemical Name: Boc-Asp(OBzl)-OSu
• CAS No.: 13798-75-9
• Molecular Formula: C20H24N2O8
• Molecular Weight: 420.419
• DSSTox Substance ID: DTXSID20542775
• Nikkaji Number: J2.856.014A
• Wikidata: Q72448541
• Mol file: 13798-75-9.mol

Synonyms:Boc-Asp(OBzl)-OSu;13798-75-9;Boc-Asp(ObBzl)-OSu;4-O-benzyl 1-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate;4-O-benzyl 1-O-(2,5-dioxopyrrolidin-1-yl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate;Boc-Asp(OBzl)O Su;DTXSID20542775;KEULITJLZYZYPU-AWEZNQCLSA-N;MFCD00037912;AKOS016014414;HY-W142110;BS-21306;L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-(2,5-dioxo-1-pyrrolidinyl) 4-(phenylmethyl) ester;Boc-Asp(OBzl)-OSu, >=98.0% (C/N);CS-0201894;J-007086;Boc-L-Aspartic acid 4-benzyl 1-(hydroxysuccinimide)ester;4-benzyl 1-(2,5-dioxopyrrolidin-1-yl) (tert-butoxycarbonyl)-l-aspartate;4-Benzyl 1-(2,5-dioxopyrrolidin-1-yl) N-(tert-butoxycarbonyl)-L-aspartate;(S)-4-benzyl 1-(2,5-dioxopyrrolidin-1-yl) 2-(tert-butoxycarbonylamino)succinate;N-alpha-t-Butyloxycarbonyl-L-aspartic acid alpha-succinimidyl beta-benZyl ester (Boc-L-Asp(OBZl)-OSu)

Chemical Property of Boc-Asp(OBzl)-OSu

Chemical Property:

• Melting Point: 98-102 °C
• Refractive Index: 1.559
• PKA: 10.22±0.46(Predicted)
• PSA: 128.31000
• Density: 1.32g/cm3
• LogP: 1.94920
• Storage Temp.: −20°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 420.15326573
• Heavy Atom Count: 30
• Complexity: 663

Purity/Quality:

98%,99%, ^*data from raw suppliers

BOC-ASP(OBZL)-OSU ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC(=O)OCC1=CC=CC=C1)C(=O)ON2C(=O)CCC2=O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC(=O)OCC1=CC=CC=C1)C(=O)ON2C(=O)CCC2=O

Technology Process of Boc-Asp(OBzl)-OSu

There total 4 articles about Boc-Asp(OBzl)-OSu 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%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → Nα-t-butoxycarbonylaspartic acid α-N-hydroxysuccinimide ester β-benzyl ester (13798-75-9)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 18h;

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → Nα-t-butoxycarbonylaspartic acid α-N-hydroxysuccinimide ester β-benzyl ester (13798-75-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sulfuric acid / diethyl ether / 48 h / 20 °C

1.2: 24 h / 0 - 20 °C

2.1: sodium hydroxide / water; 1,4-dioxane / 2 h / 0 - 20 °C

3.1: dicyclohexyl-carbodiimide / tetrahydrofuran / 18 h / 0 °C

With sulfuric acid; dicyclohexyl-carbodiimide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water;

Reference yield:

(S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid (2177-63-1,25248-99-1) → Nα-t-butoxycarbonylaspartic acid α-N-hydroxysuccinimide ester β-benzyl ester (13798-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water; 1,4-dioxane / 2 h / 0 - 20 °C

2: dicyclohexyl-carbodiimide / tetrahydrofuran / 18 h / 0 °C

With dicyclohexyl-carbodiimide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; water;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

BOC-L-aspartic acid 4-benzyl ester

benzyl alcohol

(S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid

Downstream raw materials:

Boc-Asp(OBzl)-Ala-OH

Boc-Asp(OBzl)-Pro-OH

diketopiperazine of L-aspartic acid dibenzyl ester

((S)-4-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoyl)-L-leucine

Refernces

• 1、 -. "DIPEPTIDE MIMETICS OF NGF AND BDNF NEUROTROPHINS". Paragraph 0171; 0172. . Retrieved 2019/04/16.
• 2、 Cal, Marta,Jaremko, Mariusz,Jaremko, Lukasz,Stefanowicz, Piotr. "Solid phase synthesis of peptide hydroxamic acids on poly(ethylene glycol)-based support". . p. 9 - 15. Retrieved 2013/02/25.