(2S)-2-[[(Benzyloxy)carbonyl]aMino]-5-hexenoic Acid tert-Butyl Ester

Base Information

• Chemical Name: (2S)-2-[[(Benzyloxy)carbonyl]aMino]-5-hexenoic Acid tert-Butyl Ester
• CAS No.: 127623-77-2
• Molecular Formula: C18H25NO4
• Molecular Weight: 319.401
• Mol file: 127623-77-2.mol

Synonyms:(2S)-2-[[(Benzyloxy)carbonyl]amino]-5-hexenoic Acid tert-Butyl Ester;

Chemical Property of (2S)-2-[[(Benzyloxy)carbonyl]aMino]-5-hexenoic Acid tert-Butyl Ester

Chemical Property:

• PSA: 64.63000
• LogP: 3.98020
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

(2S)-2-[[(Benzyloxy)carbonyl]amino]-5-hexenoicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S)-2-[[(Benzyloxy)carbonyl]amino]-5-hexenoic Acid tert-Butyl Ester is a reactant used in the preparation of the two collagen cross-links pyridinoline and deoxypyridinoline. It is also used in the preparation of acyl derivatives of N-hydroxypyridine-2-thione.

Technology Process of (2S)-2-[[(Benzyloxy)carbonyl]aMino]-5-hexenoic Acid tert-Butyl Ester

There total 11 articles about (2S)-2-[[(Benzyloxy)carbonyl]aMino]-5-hexenoic Acid tert-Butyl 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: 85.0%

benzyl chloroformate (501-53-1,94274-21-2) + tert-butyl (2S)-2-aminohex-5-enoate (606148-70-3) → tert-butyl (S)-2-benzyloxycarbonylamino-6-hydroxyhex-5-enoate (127623-77-2)

Guidance literature:

In 1,4-dioxane; water; at 20 ℃; for 2.5h;

DOI:10.1016/S0957-4166(03)00400-2

Reference yield: 42.0%

Nα-(Benzyloxycarbonyl)-L-lysine tert-butyl ester (112157-39-8) → tert-butyl (S)-2-benzyloxycarbonylamino-6-hydroxyhex-5-enoate (127623-77-2) + tert-butyl (S)-2-(((benzyloxy)carbonyl)amino)-6-hydroxyhexanoate (495401-20-2)

Guidance literature:

Nα-(Benzyloxycarbonyl)-L-lysine tert-butyl ester; With sodium nitrite; In water; acetic acid; at 20 ℃; for 4h;

With potassium hydroxide; In methanol;

DOI:10.1016/S0957-4166(02)00477-9

Reference yield: 28.0%

2-((S)-1-(benzyloxycarbonylamino)-2-tert-butoxy-2-oxoethyl)pent-4-enoic acid (144787-23-5) → tert-butyl (S)-2-benzyloxycarbonylamino-6-hydroxyhex-5-enoate (127623-77-2)

Guidance literature:

With 1-oxa-2-oxo-3-thiaindolizinium chloride; 2-methylpropan-2-thiol; In benzene; for 4h; Heating; Irradiation;

DOI:10.1016/S0040-4020(01)85140-1

upstream raw materials:

2-((S)-1-(benzyloxycarbonylamino)-2-tert-butoxy-2-oxoethyl)pent-4-enoic acid

Methyltriphenylphosphonium bromide

(S)-2-Benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester

Nα-(Benzyloxycarbonyl)-L-lysine tert-butyl ester

Downstream raw materials:

tert-butyl 2-benzyloxycarbonylamino-4-(2-oxiranyl)butanoate

(2S)-2-([(benzyloxy)carbonyl]amino)hex-5-enoic acid

tert-butyl (S)-2-(((benzyloxy)carbonyl)amino)-6-hydroxyhexanoate

tert-butyl (2S)-2-benzyloxycarbonylamino-6-bromo-5-hydroxyhexanoate

Refernces

• 1、 -. "Inhibitors of IAP". Page/Page column 39. . Retrieved 2010/02/15.
• 2、 Allevi, Pietro,Galligani, Matteo,Anastasia, Mario. "A simple and convenient transformation of L-lysine into pyridinoline and deoxypyridinoline, two collagen cross-links of biochemical interest". . p. 1901 - 1910. Retrieved 2007/10/03.