O-tert-Butyl-D-serine t-butyl ester hydrochloride
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O-tert-Butyl-D-serine t-butyl ester hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-003561
CAS number
179559-35-4
Molecular Formula
C11H23NO3·HCl
Molecular Weight
253.80
O-tert-Butyl-D-serine t-butyl ester hydrochloride
IUPAC Name
tert-butyl (2R)-2-amino-3-[(2-methylpropan-2-yl)oxy]propanoate;hydrochloride
Synonyms
D-Ser(tBu)-OtBu HCl
Appearance
White powder
Purity
≥ 98% (TLC)
Melting Point
170-176 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H23NO3.ClH/c1-10(2,3)14-7-8(12)9(13)15-11(4,5)6;/h8H,7,12H2,1-6H3;1H/t8-;/m1./s1
InChI Key
RDWZQVGVBTYCBD-DDWIOCJRSA-N
Canonical SMILES
CC(C)(C)OCC(C(=O)OC(C)(C)C)N.Cl
1.Synthesis of imidazol-1-yl-acetic acid hydrochloride: a key intermediate for zoledronic acid.
Singh SK1, Manne N, Ray PC, Pal M. Beilstein J Org Chem. 2008;4:42. doi: 10.3762/bjoc.4.42. Epub 2008 Nov 17.
A convenient and practical synthesis of imidazol-1-yl-acetic acid hydrochloride was achieved via N-alkylation of imidazole using tert-butyl chloroacetate followed by a non-aqueous ester cleavage of the resulting imidazol-1-yl-acetic acid tert-butyl ester in the presence of titanium tetrachloride. The synthesized imidazol-1-yl-acetic acid hydrochloride was then utilized to prepare zoledronic acid.
2.Atomic force microscopy based thermal lithography of poly(tert-butyl acrylate) block copolymer films for bioconjugation.
Duvigneau J1, Schönherr H, Vancso GJ. Langmuir. 2008 Oct 7;24(19):10825-32. doi: 10.1021/la801337f. Epub 2008 Aug 30.
In this paper, we report on the local thermal activation of thin polymer films for area-selective surface chemical modification on micrometer and nanometer length scales. The thermally induced activation of tert-butyl ester moieties in polystyrene- block-poly(tert-butyl acrylate) (PS- b-PtBA) block copolymer films leads to the formation of pending carboxylic acid groups, which are among the versatile functionalities for subsequent bioconjugation. From Fourier transform infrared (FTIR) spectroscopic analyses, the apparent activation energy (Ea) for the tert-butyl ester deprotection in thin films was calculated to be 93 +/- 12 kJ/mol, which is in good agreement with values reported for the bulk. The availability of the deprotected carboxylic acid groups in subsequent wet chemical grafting reactions on neat thermolyzed films was confirmed by covalently immobilizing fluoresceinamine and amino end-functionalized poly(ethylene glycol) (PEG-NH2) using established 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC)/N-hydroxysuccinimide (NHS) chemistry.
3.Asymmetric synthesis of (1R,2S,3R)-3-methylcispentacin and (1S,2S,3R)-3-methyltranspentacin by kinetic resolution of tert-butyl (+/-)-3-methylcyclopentene-1-carboxylate.
Bunnage ME1, Chippindale AM, Davies SG, Parkin RM, Smith AD, Withey JM. Org Biomol Chem. 2003 Nov 7;1(21):3698-707.
Conjugate addition of lithium dibenzylamide to tert-butyl (+/-)-3-methylcyclopentene-1-carboxylate occurs with high levels of stereocontrol, with preferential addition of lithium dibenzylamide to the face of the cyclic alpha,beta-unsaturated acceptor anti- to the 3-methyl substituent. High levels of enantiorecognition are observed between tert-butyl (+/-)-3-methylcyclopentene-1-carboxylate and an excess of lithium (+/-)-N-benzyl-N-alpha-methylbenzylamide (10 eq.) (E > 140) in their mutual kinetic resolution, while the kinetic resolution of tert-butyl (+/-)-3-methylcyclopentene-1-carboxylate with lithium (S)-N-benzyl-N-alpha-methylbenzylamide proceeds to give, at 51% conversion, tert-butyl (1R,2S,3R,alphaS)-3-methyl-2-N-benzyl-N-alpha-methylbenzylaminocyclopentane-1-carboxylate consistent with E > 130, and in 39% yield and 99 +/- 0.5% de after purification. Subsequent deprotection by hydrogenolysis and ester hydrolysis gives (1R,2S,3R)-3-methylcispentacin in > 98% de and 98 +/- 1% ee.
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