Allylic protection of thiols and cysteine: I: The allyloxycarbonylaminomethyl group

DOI: 10.1016/S0040-4020(99)00322-1

Source and publish data:

Tetrahedron p. 6931 - 6944 (1999)

Update date:2022-08-04

Topics:

Authors:

Kimbonguila, Andre Malanda

Merzouk, Ahmed

Guibe, Francois

Loffet, Albert

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/S0040-4020(99)00322-1

S-allyloxycarbonylaminomethyl derivatives of thiols in general and cysteine in particular are readily deprotected by palladium catalysed hydrostannolysis with tributyltin hydride in the presence of acetic acid. They are perfectly stable in the basic conditions (piperidine/DMF) of Fmoc group removal but tend to decompose, albeit slowly, in the acidic conditions (TFA/CH₂Cl₂) of t-Bu and Boc groups removal.

Full text of DOI:10.1016/S0040-4020(99)00322-1

Products guided by the article

Product name:[1-benzylcarbamoyl-2-(2-benzylcarbamoyl-2-tert-butoxycarbonylamino-ethyldisulfanyl)-ethyl]-carbamic acid tert-butyl ester

Cas No:160978-35-8

R&D Labs maybe for 160978-35-8

Hunan Haili Chemical Industry Co.,Ltd.

Contact:+86-731-85521860

Address:No.251, 2nd Section, Furong Road, Changsha,Hunan,China
shijiazhuang baisheng chem co.; ltd

Contact:86-0311-80790826

Address:shijiazhuang hebei
Shanghai agrotree chemical co.,ltd.

Contact:+86-21-50117563

Address:Room 8A,liangfeng building,No.8 dongfang RD.pudong,shanghai,China
Huaian Double Win Chemicals Co.,Ltd.

Contact:+86-13511538872

Address:Blk 43,Greenland Century Town,Huaian District, Huaian City,Jiangsu Province,China
MTT Pharma & Bio-technology Co.,Ltd(expird)

Contact:+86-21-58407925

Address:Room2019, Building C, Tomson Center, No.158, Zhang Yang Road, Shanghai, China

Relevant to this article

Synthesis of 2′-O,4′-C-alkylene-bridged ribonucleosides and their evaluation as inhibitors of HCV NS5B polymerase

Doi:10.1016/j.bmcl.2014.04.050
(2014)
Discovery of lipoic acid-4-phenyl-1: H -pyrazole hybrids as novel bifunctional ROCK inhibitors with antioxidant activity

Doi:10.1039/c6ra12081d
(2016)
Synthesis of silicon-functionalized (silylmethyl)silanes and-dichlorocarbosilanes using the TMOP (2,4,6-trimethoxyphenyl) protecting group: (TMOP)Me2SiCH2Cl and (TMOP) 2MeSiCH2Cl as reagents to introduce the ClMe 2SiCH2, MeOMe2SiCH2, or Cl2MeSiCH2 group by nucleophilic substitution at silicon

Doi:10.1021/om400190q
(2013)
Synthesis and biological evaluation of novel quinazoline-triazole hybrid compounds with potential use in Alzheimer's disease

Doi:10.1016/j.bmcl.2020.127404
(2020)
Towards the development of 5-HT₇ ligands combining serotonin-like and arylpiperazine moieties

Doi:10.1016/j.ejmech.2014.04.034
(2014)
Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog

Doi:10.3762/bjoc.10.29
(2014)

Article Doi