Synthesis of (S)-3-Phenylpropane-2-tert-butoxycarbonylamino- 1-thiol and its Electrochemical Behavior Self-assembled on Gold

Authors

SUN Ru, 1), GE Jian-feng~(2), WANG Mei~(1),GU Ren-ao~(*1) (1. Department of Chemistry and Chemical Engineering, Suzhou University,Jiangsu 215006, China 2.~( )Department of Material and Engineering,Suzhou University, Jiangsu 215006,China;

Abstract

The synthesis of (S)-3-Phenylpropane-2-tert-butoxycarbonylamino- 1-thiol(N-Boc-APT) from L-phenylalanine was reported. L-Phenylalanine was reduced to the corresponding amino alcohol, protection of the amino group using tert-butyl pyrocarbonate gave (S)-2-tert-butoxycarbonylamino-3-phenylpropane-1-ol, which was then O-mesylated and treated with potassium thioacetate in DMF to give 3-phenylpropane-2-tert- butoxycarbonylamino-1-etylmercapto. After the acetyl group was removed with ammonia in alcohol, the desired target molecular was obtained. The structure of intermediate and target molecular was conformed by IR and ~(1)HNMR. We made N-Boc-APT self-assemble-modificated gold electrode and investigated its electrochemical behavior. The CV results of methylene blue on nano-Au/N-Boc-APT SAM/Au electrode showed that nano-Au could speed this electron transfer process.

Keywords

(S)-3-Phenylpropane-2-tert-butoxycarbonylamino-1-thiol, Asymmetric synthesis, Self-assembled, Electrochemistry, Gold nanoparticals, Methylene blue

DOI Link

https://doi.org/10.61558/2993-074X.1579

Publication Date

2004-08-28

Online Available Date

2004-08-28

Revised Date

2004-08-28

Received Date

2004-08-28

Recommended Citation

SUN Ru. Synthesis of (S)-3-Phenylpropane-2-tert-butoxycarbonylamino- 1-thiol and its Electrochemical Behavior Self-assembled on Gold[J]. Journal of Electrochemistry, 2004 , 10(3): 307-313.
DOI: 10.61558/2993-074X.1579
Available at: https://jelectrochem.xmu.edu.cn/journal/vol10/iss3/9

References

[1]HulstR,HeresH,PeterNCMW,etal.Synthesisandapplicationofnewchiralligandsfortheasymmetricboranereductionofprochiralketones[J].Tetrahedron:Asymmetry,1996,7(5):1373.
[2]FroelichO,BoninM,QuirionJC,etal.Diazaborolidines,anewclassofenantioselectiveorganoboroncatalyticagents[J].Tetrahedron:Asymmetry,1993,4(11):2335.
[3]　HandrickGR,AtkinsonER,GranchelliFE,etal.Potentialantiradiationdrugs.Ⅱ.2 amino 1 alkanethiols,1amino 2 alkanethiols,2 thiazolines,and2 thiazoline 2 thiols[J],J.Med.Chem.,1965,8:762.
[4]　MckennonMJ,MeyersAI,KarlheinzD,etal.AConvenientrductionofainoaidsandteirdrivatives[J].J.Org.Chem.,1993,58(13):3568.
[5]　DaytonMA,BrownJC,StuttsKJ,etal.Faradaicelectrochemistryatmicrovoltammetricelectrodes[J].Anal.Chem.,1980,52:946.
[6]　KaufmanFB,SchroederAH,EnglerEM,etal.IonandElectronTransportinStable,Electroactivetetrathiafulvalenepolymercoatedelectrodes[J].J.Am.Chem.Soc.,1980,102(2):483.
[7]　WongSS,PorterMD.Originofthemultiplevoltammetricdesorptionwavesoflong chainalkanethiolatemonolayerschemisorbedonannealedgoldelectrodes[J].J.Electroanal.Chem.,2000,485:135.
[8]　ZhaoFQ,ZengBCh,PangDW,VoltammetricstudyofmethyleneblueatthiolSAMs modifiedgoldelectrodes[J].Electroanalysis,2003,15(12):1060.
[9]　SagaraT,KawamuraH,NakashimaN,etal.Electrodereactionofmethyleneblueatanalkanethiol modifiedgoldelectrodeascharacterizedbyelectroreflectancespectroscopy[J].Langmuir,1996,12:4253.