TERT-BUTYL 2-(TERT-BUTOXYCARBONYLAMINO)-4-(OXIRAN-2-YL)BUTANOATE

Base Information

• Chemical Name: TERT-BUTYL 2-(TERT-BUTOXYCARBONYLAMINO)-4-(OXIRAN-2-YL)BUTANOATE
• CAS No.: 220243-56-1
• Molecular Formula: C₁₅H₂₇NO₅
• Molecular Weight: 301.383
• Mol file: 220243-56-1.mol

Synonyms:tert-Butyl 2-(tert-butoxycarbonylamino)-4-(oxiran-2-yl)butanoate;Hexonic acid, 5,6-anhydro-2,3,4-trideoxy-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester;

Chemical Property of TERT-BUTYL 2-(TERT-BUTOXYCARBONYLAMINO)-4-(OXIRAN-2-YL)BUTANOATE

Chemical Property:

• Vapor Pressure: 1.84E-06mmHg at 25°C
• Refractive Index: 1.47
• Boiling Point: 395.4 °C at 760 mmHg
• Flash Point: 192.9 °C
• PSA: 77.16000
• Density: 1.077 g/cm³
• LogP: 2.79130

Purity/Quality:

99% ^*data from raw suppliers

TERT-BUTYL-2-((TERT-BUTOXYCARBONYL)AMINO)-4-(OXIRAN-2-YL)BUTANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TERT-BUTYL 2-(TERT-BUTOXYCARBONYLAMINO)-4-(OXIRAN-2-YL)BUTANOATE

There total 3 articles about TERT-BUTYL 2-(TERT-BUTOXYCARBONYLAMINO)-4-(OXIRAN-2-YL)BUTANOATE 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: 91.0%

(+/-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-5-hexenoate (151294-93-8) → (+/-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-(2-oxiranyl)butanoate (220243-56-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1016/S0040-4020(98)01023-0

Reference yield:

N-(tert-butoxycarbonyl)glycine tert-butyl ester (111652-20-1) → (+/-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-(2-oxiranyl)butanoate (220243-56-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi; HMPA / tetrahydrofuran / -78 °C

1.2: 86 percent / tetrahydrofuran / 7.5 h / -78 - 20 °C

2.1: 91 percent / m-CPBA / CH₂Cl₂ / 17 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 1.1: Metallation / 1.2: Alkylation / 2.1: Epoxidation;

DOI:10.1016/S0040-4020(98)01023-0

Reference yield:

→ (+/-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-(2-oxiranyl)butanoate (220243-56-1)

Guidance literature:

upstream raw materials:

(+/-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-5-hexenoate

N-(tert-butoxycarbonyl)glycine tert-butyl ester

Downstream raw materials:

(+/-)-di(tert-butyl) 11-benzyl-9,13-dihydroxy-2,2,20,20-tetramethyl-4,18-dioxo-3,19-dioxa-5,11,17-triazahenicosane-6,16-dicarboxylate

Refernces

• 1、 Adamczyk, Maciej,Johnson, Donald D.,Reddy, Rajarathnam E.. "Collagen cross-links: Synthesis of pyridinoline, deoxypyridinoline and their analogues". . p. 63 - 88. Retrieved 2007/10/03.