161392-58-1

Basic information

• Product Name: 3,4-bis(tert-butyldimethylsilyloxy)-L-phenylalanine
• Synonyms: 3,4-bis(tert-butyldimethylsilyloxy)-L-phenylalanine
• CAS NO: 161392-58-1
• Molecular Weight: 425.716
• Mol File: 161392-58-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3,4-bis(tert-butyldimethylsilyloxy)-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-bis(tert-butyldimethylsilyloxy)-L-phenylalanine(161392-58-1)
• EPA Substance Registry System: 3,4-bis(tert-butyldimethylsilyloxy)-L-phenylalanine(161392-58-1)

Safety Data

• Hazardous Substances Data: 161392-58-1(Hazardous Substances Data)

Upstream product

• 364619-17-0 3,4-bis(tert-butyldimethylsilyloxy)-N-(9-fluorenylmethyloxycarbonyl)-L-phenylalanine 
• 59-92-7 levodopa 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 161392-63-8 Boc-L-DOPA(TBDMS)2-Phe-OtBu 
• 161392-62-7 (S)-2-{(S)-3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionylamino}-4-methyl-pentanoic acid tert-butyl ester 
• 161392-64-9 (S)-2-{(S)-3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionylamino}-3-methyl-butyric acid tert-butyl ester 
• 364619-18-1 3,4-bis(tert-butyldiphenylsilyloxy)-N-tert-butyloxycarbonyl-L-phenylalanine 
• 364619-20-5 3,4-bis(tert-butyldiphenylsilyloxy)-L-phenylalanine 
• 30033-24-0 (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoic acid 
• 364619-17-0 3,4-bis(tert-butyldimethylsilyloxy)-N-(9-fluorenylmethyloxycarbonyl)-L-phenylalanine 
• 267001-18-3 Fmoc-Thr(O-t-Bu)-DOPA(OTBS)2-OH 
• 158955-67-0 (2S)-3-[3,4-bis[(tert-butyldimethylsilyl)oxy]phenyl]-2-[(tert-butoxycarbonyl)amino]propanoic acid 

Relevant articles and documents

COMPOSITIONS AND METHODS FOR SINGLE-STEP MULTIPURPOSE SURFACE FUNCTIONALIZATION

Compositions and methods for functionalizing a variety of surfaces are provided herein. The compositions include compounds of formula (I), which react with azido compounds (R-N3) to form cycloadducts that can spontaneously polymerize on a surfa

Water-soluble L-DOPA esters

The present invention relates to novel compounds of the formula I, methods for their preparation and their use for treatment of diseases. The invention discloses the synthesis of levodopa (L-DOPA) esters by coupling polyhydroxy compounds or their derivatives to the L-DOPA carboxyl group. The synthesis allows to produce L-DOPA derivatives which are highly soluble in water as well as aqueous and biocompatible liquids and have an improved hydrolytic stability in water or aqueous and biocompatible media for an application over several days. The invention helps producing L-DOPA substances for applications in the fields of medicine, biology and medical engineering as well as in the pharmaceutical industry.

Synthesis of peptides containing DOPA (3,4-dihydroxyphenylalanine)

Proteins from coral reefs structures, eggshells, and marine mollusk adhesives all contain the amino acid 3,4-dihydroxyphenylalanine (DOPA). The insoluble nature of these materials has hampered characterization and turned our efforts toward work with small peptide mimics. In this paper, we present the syntheses of various DOPA derivatives: Boc-DOPA, Fmoc-DOPA, DOPA(TBDMS)2, DOPA(TBDPS)2, Boc-DOPA(TBDPS)2, Fmoc-DOPA(TBDMS)2, and Fmoc-DOPA(TBDPS)2 (where Boc=tert-butyloxycarbonyl, Fmoc=9-fluorenylmethyloxycarbonyl, TBDMS=tert-butyldimethylsilyl, and TBDPS=tert-butyldiphenylsilyl). These DOPA compounds were used to prepare peptides of various sequences. The synthetic procedure described provides an efficient route to DOPA-containing peptides in which sidechain deprotection and cleavage from resin can be accomplished in one step.