cas 79069-15-1, N-Boc-(S)-2-amino-3-benzyloxy-1-propanol

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Iterative Synthesis of Stereo- and Sequence-Defined Polymers via Acid-Orthogonal Deprotection Chemistry
Absolute control over polymer stereo- and sequence structure is highly challenging in polymer chemistry. Here, an acid-orthogonal deprotection strategy is proposed for the iterative synthesis of a family of unimolecular polymers starting with enantiopure
He, Wenjing,Li, Maosheng,Tao, Youhua,Wang, Shixue,Wang, Xianhong
(2022/01/20)

DEUTERATED COMPOUNDS FOR USE IN THE TREATMENT OF CANCER
The application relates to deuterated amide derivatives of formula (I) and their use in the treatment and prophylaxis of cancer, and to compositions containing said derivatives and processes for their preparation.
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(2021/02/19)

Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production
The piperazine heterocycle is broadly exploited in FDA-approved drugs and biologically active compounds, but its chemical diversity is usually limited to ring nitrogen substitutions, leaving the four carbon atoms underutilized. Using an efficient six-step synthesis, chiral amino acids were transformed into 3-substituted piperazine-2-acetic acid esters as diastereomeric mixtures whose cis and trans products (dr 0.56 a? 2.2:1, respectively) could be chromatographically separated. From five amino acids (both antipodes) was obtained a complete matrix of 20 monoprotected chiral 2,3-disubstituted piperazines, each as a single absolute stereoisomer, all but one in multigram quantities. In keeping with our overall purpose of constructing more Csp3-enriched compound libraries for drug discovery, these diverse and versatile piperazines can be functionalized on either nitrogen atom, allowing them to be used as scaffolds for parallel library synthesis and as intermediates for the production of novel piperazine compounds.
Reddy Guduru, Shiva Krishna,Chamakuri, Srinivas,Raji, Idris O.,MacKenzie, Kevin R.,Santini, Conrad,Young, Damian W.
p. 11777 - 11793
(2018/09/27)

TRICYCLIC 2-QUINOLINONES AS ANTIBACTERIALS
This invention is in the field of medicinal chemistry and relates to compounds, and pharmaceutical compositions thereof that are useful as antibacterial agents. The compounds are useful as inhibitors of bacterial gyrase activity and of bacterial infections, and have the structure of Formula (I): as further described herein. The invention further provides pharmaceutical compositions comprising a compound of Formula (I) and methods of using the compounds and compositions to treat bacterial infections.
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Paragraph 00225; 00226

(2018/11/26)

LPA5 RECEPTOR AGONIST
PROBLEM TO BE SOLVED: To provide a drug containing as an active ingredient a compound having agonist activity for an LPA5 receptor in disease caused by the LPA5 receptor. SOLUTION: A compound represented by general formula (I) in the figure, where all symbols refer to the same as those described in the specification, or a pharmaceutically acceptable salt thereof is useful as a drug component having agonist activity for an LPA5 receptor in prevention and/or treatment of disease caused by the LPA5 receptor, e.g., digestive system disease, immune system disease or cancer. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0219; 0220

(2018/07/31)

Effects of the Backbone and Chemical Linker on the Molecular Conductance of Nucleic Acid Duplexes
Scanning tunneling microscope break junction measurements are used to examine how the molecular conductance of nucleic acids depends on the composition of their backbone and the linker group to the electrodes. Molecular conductances of 10 base pair long h
Beall, Edward,Ulku, Selma,Liu, Chaoren,Wierzbinski, Emil,Zhang, Yuqi,Bae, Yookyung,Zhang, Peng,Achim, Catalina,Beratan, David N.,Waldeck, David H.
p. 6726 - 6735
(2017/05/29)

A multifaceted secondary structure mimic based on piperidine-piperidinones
Minimalist secondary structure mimics are typically made to resemble one interface in a protein-protein interaction (PPI), and thus perturb it. We recently proposed suitable chemotypes can be matched with interface regions directly, without regard for secondary structures. Here we describe a modular synthesis of a new chemotype 1, simulation of its solution-state conformational ensemble, and correlation of that with ideal secondary structures and real interface regions in PPIs. Scaffold 1 presents amino acid side-chains that are quite separated from each other, in orientations that closely resemble ideal sheet or helical structures, similar non-ideal structures at PPI interfaces, and regions of other PPI interfaces where the mimic conformation does not resemble any secondary structure. 68 different PPIs where conformations of 1 matched well were identified. A new method is also presented to determine the relevance of a minimalist mimic crystal structure to its solution conformations. Thus dld-1-faf crystallized in a conformation that is estimated to be 0.91 kcal-mol-1 above the minimum energy solution state. Do we know, when designing a new peptidomimetic scaffold like the one shown, how it can resemble secondary structures? Design and modular synthesis of this elongated mimic is reported, and the structure is related to ideal and real structures at PPI interfaces.
Xin, Dongyue,Perez, Lisa M.,Ioerger, Thomas R.,Burgess, Kevin
p. 3594 - 3598
(2014/04/17)

A mild multistep conversion of n-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction
Current methods of homologation of α-amino acids to β-amino acids have limitations. To overcome these shortfalls the Nef reaction has been utilized in the multistep synthesis of β3-amino acids from α-amino acids. In this approach, N-protected a
Sleebs, Brad E.,Nguyen, Nghi H.,Hughes, Andrew B.
supporting information
p. 747 - 751
(2013/05/08)

Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists
To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified γ-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the γ-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented.
Kambe, Tohru,Maruyama, Toru,Nagase, Toshihiko,Ogawa, Seiji,Minamoto, Chiaki,Sakata, Kiyoto,Maruyama, Takayuki,Nakai, Hisao,Toda, Masaaki
p. 702 - 713
(2012/03/11)

Novel branched isocyanides as useful building blocks in the Passerini-amine deprotection-acyl migration (PADAM) synthesis of potential HIV-1 protease inhibitors
Novel branched isocyanides have been prepared from l-serine and used as building blocks in the Passerini-amine deprotection-acyl migration (PADAM) sequence for the preparation of compounds with activity against HIV-1 protease.
Gravestock, David,Rousseau, Amanda L.,Lourens, Anna C.U.,Hoppe, Heinrich C.,Nkabinde, Lindiwe A.,Bode, Moira L.
p. 3225 - 3229
(2012/07/31)

Synthesis of threo-β-aminoalcohols from aminoaldehydes via chelation-controlled additions. Total synthesis of l-threo sphingosine and safingol
Chelation-controlled addition of organocuprates to N-carbamoyl aminoaldehydes, prepared from functionalized amino acids, generated predominately the threo-β-amino alcohol derivatives through chelation with the carbamoyl moiety. The carbamate group is a stronger chelating group than other potentially good chelators, for example ethers, esters, thioethers, and gives good diastereoselectivity with cuprates. Thus addition of lithium divinylcuprate to the aldehyde generated from the serine derivative 25 in the presence of extra copper for chelation afforded the threo compound 26 in 83% yield. Cross-metathesis and cleavage of the protecting groups furnished l-threo sphingosine 21. In addition the lyso-sphingolipid protein kinase C inhibitor, safingol, 22, was prepared from commercially available O-benzyl N-BOC serine 28 in six steps and 56% overall yield by this method.
Jung, Michael E.,Yi, Sung Wook
supporting information; experimental part
p. 4216 - 4220
(2012/08/29)

NOVEL COMPOUNDS FOR MEDICAL USE AS PEPTIDASE EFFECTORS
The invention relates to compounds of general formula (I) as set forth in the claims as well as to the use of the compounds of the general formula (1) in the medical field, specifically for use in the suppression of DNA synthesis and inflammatory cytokine production as well as in the stimulation of anti-inflammatory cytokine production in vitro and in vivo. This abstract is neither intended to define the invention disclosed in this specification nor intended to limit the scope of the invention in any way.
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Page/Page column 70

(2012/02/06)

CATHEPSIN S INHIBITORS
Cathepsin S inhibitors having formula (I), (II), (III) or (IV) as shown in the specification. These inhibitors can be used to treat cancer and autoimmune/inflammatory diseases.
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Page/Page column 26

(2011/06/25)

A stereoselective route to cis-(2S,3R)-3-hydroxypipecolic acid and two enantiomeric cis-2-hydroxymethyl-3-hydroxypiperidine derivatives
Stereoselective routes to cis-(2S,3R)-3-hydroxypipecolic acid and two enantiomeric cis-2-hydroxymethyl-3-hydroxypiperidine derivatives from a common precursor have been developed, which featured stereocontrolled vinylation of a -chiral aldehyde and ring-closing metathesis as key steps. Georg Thieme Verlag Stuttgart. New York.
Chattopadhyay, Shital K.,Roy, Shankar P.,Saha, Tapan
p. 2664 - 2670
(2011/10/04)

Simple and efficient synthesis of Fmoc/Boc/Cbz-protected-β-amino alcohols and peptidyl alcohols employing Boc2O
An efficient method for the activation of Fmoc/Boc/Cbz-protected amino acids using Boc2O and the reduction of the in situ generated carbonic-carbonic anhydride to their corresponding 1β-amino alcohols using sodium borohydride has been described. The method is simple, rapid and free from racemization. Besides, the protocol is also extended for the conversion of N-urethane protected peptide acids to their corresponding alcohols. Copyright
Lalithamba,Sureshbabu, Vommina V.
experimental part
p. 1372 - 1378
(2011/01/13)

Simple and rapid synthesis of Nα-urethane protected β-amino alcohols and peptide alcohols employing HATU
The activation of the Nα--urcihanc protected (Fmoc-/Boc-/Z-/Bsmoc) α-amino acids employing l-[bis(dimethylamino)- methylene]-lH-l,2,3-triazolo-[4,5-6]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the in situ generated -OAt ester with NaBH 4 results in the corresponding ss-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent HATU for practical synthesis of ss-amino alcohols. The protocol is general for all common N-protecting groups including the highly base sensitive Bsmoc group. The protocol has also been successfully extended for the synthesis of peptide alcohols.
Surcshbabu, Vommina V.,Sudarshan,Chennakrishnareddy
experimental part
p. 574 - 579
(2009/12/06)

syn-Selective dihydroxylation of γ-amino-α,β-unsaturated (Z)-esters from d-serine: stereoselective synthesis of d-iminolyxitol
An efficient and stereoselective synthesis of d-iminolyxitol, a potent α-galactosidase inhibitor, is achieved in 11 steps over 45% overall yield from N-Boc-O-Bn-d-serine. The key step involves the OsO4-catalyzed syn-selective dihydroxylation re
Jeon, Jongho,Lee, Jong Hyup,Kim, Jung-Won,Kim, Young Gyu
p. 2448 - 2453
(2008/03/13)

Synthesis of N-urethane protected β-amino alcohols employing N-(protected-α-aminoacyl)benzotriazoles
A simple and racemisation-free synthesis of N-urethane protected α-amino/peptidyl alcohols by the reduction of the corresponding easily accessible N-acylbenzotriazoles is described. The method is practical, straightforward, fast and efficient for the synt
Sureshbabu, Vommina V.,Sudarshan,Muralidhar,Narendra
p. 683 - 685
(2008/09/20)

Reduction of pentafluorophenyl esters to the corresponding primary alcohols using sodium borohydride
Primary alcohols and chiral N-protected 2-amino alcohols can be obtained in high yields from the reaction of pentafluorophenyl esters of the corresponding carboxylic acids with sodium borohydride in THF under mild conditions. This reductive method is rapid and compatible with various functional groups as well as with the most common N-protective groups Z, Boc and Fmoc.
Papavassilopoulou, Eleni,Christofis, Petros,Terzoglou, Despina,Moutevelis-Minakakis, Panagiota
p. 8323 - 8325
(2008/04/13)

Arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 2: Optimization of P1 and N-aryl
A systematic study of anilines led to the discovery of a metabolically robust fluoroindoline replacement for the alkoxy aniline toxicophore in 1. Investigations of the P1 pocket resulted in the discovery of a wide tolerance of functionality leading to the discovery of 11 as a potent and selective inhibitor of cathepsin S.
Alper, Phillip B.,Liu, Hong,Chatterjee, Arnab K.,Nguyen, Khanhlinh T.,Tully, David C.,Tumanut, Christine,Li, Jun,Harris, Jennifer L.,Tuntland, Tove,Chang, Jonathan,Gordon, Perry,Hollenbeck, Thomas,Karanewsky, Donald S.
p. 1486 - 1490
(2007/10/03)

ETHER DERIVATIVE
The present invention relates to an ether derivative represented by the formula (I), a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof wherein each symbol is as defined in the description, and an ether derivative represented by the formula (III), a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof wherein each symbol is as defined in the description; a pharmaceutical composition containing the ether derivative; and a package containing the pharmaceutical composition and a description of use thereof. A pharmaceutical composition of the present invention, which contains this compound of the present invention has a superior anti-inflammatory and analgesic activity and is useful as various pharmaceutical agents such as an anti-inflammatory agent, an analgesic, a therapeutic agent for inflammatory bowel disease, a therapeutic agent for pollakiuria and/or incontinentia, a therapeutic agent for asthma and the like.
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Page/Page column 29

(2008/06/13)

ORALLY AVAILABLE SPHINGOSINE 1-PHOSPHATE RECEPTOR AGONISTS AND ANTAGONISTS
The present invention relates to S1P analogs that have activity as S1Preceptor modulating agents and the use of such compounds to treat diseases associated with inappropriate S1P receptor activity. The compounds have the general structure (I) wherein R11 is C5-C18 alkyl or C5-C18 alkenyl; Q is selected from the group consisting of C3-C6 optionally substituted cycloalkyl, C3-C6 optionally substituted heterocyclic, C3-C6 optionally substituted aryl C3-C6 optionally substituted heteroaryl and; R2 is selected from the group consisting of H, C1-C4 alkyl, (C1-C4 alkyl)OH and (C1-C4 alkyl)NH2; R23 is H or C1-C4 alkyl, and R15 is a phosphonate ester or a phosphate ester or a pharmaceutically acceptable salt or tautomer thereof.
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Page/Page column 105-106

(2008/06/13)

Regioselective cleavage of the bis-benzylidene acetal of D-mannitol under oxidative and reductive conditions: A new approach to C2-symmetric chiral ligands
A highly regioselective oxidative cleavage of 1,3:4,6-di-O-benzylidene-d- mannitol was carried out using NBS and the resultant product was readily converted to the C2-symmetric chiral ligand, (R,R)-3,4-dihydroxy-1,5- hexadiene. On the other hand, reductive cleavage of 1,3:4,6-di-O-benzylidene-d- mannitol was achieved in a highly regioselective manner using BF 3?OEt2 and Et3SiH to give a highly functionalized benzyl ether, which was converted to a synthetically useful C2-symmetric bis-amino alcohol derivative.
Aravind, Appu,Mohanty, Subhendu K.,Pratap, T. Veerabhadra,Baskaran, Sundarababu
p. 2965 - 2968
(2007/10/03)

Facile Route to 3,5-Disubstituted Morpholines: Enantioselective Synthesis of O-Protected trans-3,5-Bis(hydroxymethyl)morpholines
(Equation presented) trans-3,5-Bis(benzyl/terf-butyldiphenylsilyloxymethyl) morpholines, promising candidates for the C2-symmetric class of chiral reagents, were prepared with excellent optical purity. A key step in the synthesis is the couplin
Dave, Rajesh,Andre Sasaki
p. 15 - 18
(2007/10/03)

8-AZAPROSTAGLANDIN DERIVATIVE COMPOUNDS AND DRUGS CONTAINING THE COMPOUNDS AS THE ACTIVE INGREDIENT
An 8-azaprostaglandin represented by formula (I) (wherein all symbols have the same meanings as described in the specification), a pharmaceutically acceptable salt thereof or a cyclodextrin clathrate thereof. Since the compound represented by formula (I)
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Page 226

(2008/06/13)

Exploration of the P1 SAR of aldehyde cathepsin K inhibitors.
The synthesis and biological activity of a series of aldehyde inhibitors of cathepsin K are reported. Exploration of the properties of the S(1) subsite with a series of alpha-amino aldehyde derivatives substituted at the P(1) position afforded compounds with cathepsin K IC(50)s between 52 microM and 15 nM.
Catalano, John G,Deaton, David N,Furfine, Eric S,Hassell, Annie M,McFadyen, Robert B,Miller, Aaron B,Miller, Larry R,Shewchuk, Lisa M,Willard Jr., Derril H,Wright, Lois L
p. 275 - 278
(2007/10/03)

Synthesis and in vivo anti-inflammatory activity of long-chain 2-amino-alcohols
The synthesis of optically pure long-chain 2-amino-alcohols and 1-O-dodecyl-2-deoxy-2-amino-sn-glycerol was carried out starting from L- or D-Boc-Ser(OBn)-ol by oxidation and consecutive Wittig reaction or etherification reaction. 2-Amino-oleyl alcohol wa
Magrioti, Victoria,Hadjipavlou-Litina, Dimitra,Constantinou-Kokotou, Violetta
p. 375 - 377
(2007/10/03)

Inhibitors of protein isoprenyl transferases
Compounds having the formula or a pharmaceutically acceptable salt thereof wherein R1is (a) hydrogen, (b) loweralkyl, (c) alkenyl, (d) alkoxy, (e) thioalkoxy, (f) halo, (g) haloalkyl, (h) aryl-L2—, and (i) heterocyclic-L2—; R2is selected from (a) (b) —C(O)NH—CH(R14)—C(O)OR15, (d) —C(O)NH—CH(R14)—C(O)NHSO2R16, (e) —C(O)NH—CH(R14)-tetrazolyl, (f) —C(O)NH-heterocyclic, and (g) —C(O)NH—CH(R14)—C(O)NR17R18; R3is substituted or unsubstituted heterocyclic or aryl, substituted or unsubstituted cycloalkyl or cycloalkenyl, and —P(W)RR3RR3′; R4is hydrogen, lower alkyl, haloalkyl, halogen, aryl, arylakyl, heterocyclic, or (heterocyclic)alkyl; L1is absent or is selected from (a) —L4—N(R5)—L5—, (b) —L4—O—L5—, (c) —L4—S(O)n—L5— (d) —L4—L6—C(W)—N(R5)—L5—, (e) —L4—L6—S(O)m—N(R5)—L5—, (f) —L4—N(R5)—C(W)—L7—L5—, (g) —L4—N(R5)—S(O)p—L7—L5—, (h) optionally substituted alkylene, (i) optionally substituted alkenylene, (j) optionally substituted alkynylene (k) a covalent bond, (l) and (m) are inhibitors of protein isoprenyl transferases. Also disclosed are protein isoprenyl transferase inhibiting compositions and a method of inhibiting protein isoprenyl transferases.
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(2008/06/13)

Design and synthesis of cyclic sialyl Lewis X mimetics: A remarkable enhancement of inhibition by pre-organizing all essential functional groups
Two rigid macrocyclic glycopeptides 1 and 2 were designed to mimic the tetrasaccharide SLe(X) as inhibitors of P-selectin. While compound 1 was found to be 1000-fold more potent than SLe(X) with IC50 = 1 μM, compound 2 was not soluble in water for evaluation of its activity. (C) 2000 Elsevier Science Ltd.
Tsai,Huang,Wong
p. 9499 - 9503
(2007/10/03)

Synthesis and biophysical studies of modified oligonucleotides containing acyclic amino alcohol nucleoside analogs
Novel serine derivative of thymine was prepared and incorporated into oligonucleotides. These modified oligonucleotides were studied for their binding affinity with complementary DNA/RNA.
Ramasamy, Kanda S.,Stoisavljevic, Vesna
p. 1845 - 1861
(2007/10/03)

Oligonucleotide analogs with an amino acid or a modified amino alcohol residue
The present invention provides various novel oligonucleotide analogs having one or more properties that make the subject compounds superior to conventional oligonucleotides for use in procedures employing oligonucleotides. The compounds of the invention are oligonucleotide analogs in which the furanose ring of a naturally occurring nucleic acid is replaced with an amino acid or a modified amino alcohol residue. Some embodiments of the novel compounds of the invention are particularly useful for the antisense control of gene expression. The compounds of the invention may also be used as nucleic acid hybridization probes or as primers. Another aspect of the invention is to provide monomeric precursors of the oligonucleotide analogs of the invention. These monomeric precursors may be used to synthesize the subject polynucleotide analogs. Another aspect of the invention is to provide formulations of the subject polynucleotide analogs that are designed for the treatment or prevention of disease conditions. Yet another aspect of the invention is to provide methods for treating or preventing diseases, particularly viral infections and cell growth disorders. The subject disease treatment methods comprise the step of administering an effective amount of the subject polynucleotide analogs for use as antisense inhibitors.
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(2008/06/13)

Polyamide based nucleic acid analogs synthesis of δ-amino acids with nucleic acid bases bearing side chains
Nucleoamino acids of type I-III have been synthesized, which can serve as building blocks for novel polyamide based nucleic acid analogs. Key steps in the syntheses are the alkylation of serinol I and homoserinol 18 with tert-butyl bromoacetate or tert-butyl bromopropionate under phase transfer conditions and the introduction of thymine or uracil into the amino acid side drains by way of a Mitsunobu reaction. Cytosine derivatives were prepared through uracil → cytosine base conversion at the stage of N(δ)-BOC protected amino acid tert-butyl esters.
Altmann, Karl-Heinz,Chiesi, Chantal Schmit,Garcia-Echeverria, Carlos
p. 1119 - 1122
(2007/10/03)

Amino acid nucleic acids: Synthesis and hybridization properties of a novel class of antisense oligonucleotides
Oligonucleotides containing novel phoshoramidite 12 were synthesized and studied for their hybridization properties for the first time. Interestingly, these modified oligonucleotides showed a remarkable resistance to exonuclease.
Ramasamy, Kanda S.,Seifert, Wilfried
p. 1519 - 1522
(2007/10/03)

Convenient procedures for the synthesis of N-BOC-D-serinal acetonide from L-serine
Two straightforward synthetic routes for the preparation of enantiomerically pure N-BOC-D-serinal acetonide (enantiomer of Garner's aldehyde) starting from naturally occurring L-serine are described.
Avenoza,Cativiela,Corzana,Peregrina,Zurbano
p. 1146 - 1150
(2007/10/03)

Selective one-pot conversion of carboxylic acids into alcohols
Carboxylic acids are converted into alcohols by chemoselective reduction of their corresponding fluorides with sodium borohydride and dropwise addition of methanol. The method is general and mild and displays a high level of functional group compatibility. N-Protected amino and peptide alcohols, bearing varieties of protecting groups, are prepared in the same way from their corresponding amino acids and peptides without racemization.
Kokotos, George,Noula, Caterina
p. 6994 - 6996
(2007/10/03)

Amino acid nucleic acids: Synthesis and hybridization properties of a novel class of antisense oligonucleotides
Oligonucleotides containing novel phosphoramidite 12 were synthesized and studied for their hybridization properties for the first time. Interestingly, these modified oligonucleotides showed a remarkable resistance to exonuclease.
Ramasamy, Kanda S.,Seifert, Wilfried
p. 1799 - 1804
(2007/10/03)

Synthesis of enantiomerically pure 1-(R)- and 1-(S)-hydroxymethyl-DTPA penta-t-butyl esters via chiral aminoalcohols
A convenient synthesis of enantiomerically enriched 1-hydroxymethyl-DTPA (diethylenetriamine pentaacetic acid) penta-t-butyl esters 3 has been achieved for the preparation of chiral synthones of new paramagnetic gadolinium complexes.
Sajiki, Hironao,Ong, Karen Y.,Nadler, Samuel T.,Wages, Heather E.,McMurry, Thomas J.
p. 2511 - 2522
(2007/10/03)

Synthesis of an enantiomerically pure serine-derived thiazole
Previously reported methods for preparing enantiomerically pure thiazoles are inadequate for the synthesis of inherently labile O-alkyl serine-derived thiazoles. The intermediate N-Boc-(O-methylseryl) thiazolines are very susceptible to tautomerization, e
Sowinski, Jennifer A.,Toogood, Peter L.
p. 7671 - 7676
(2007/10/03)

Conversion of chiral amino acids to enantiomerically pure α-methylamines
Enantiomerically enriched α-methylamines are obtained in high yield by Raney nickel reduction of N-Boc-protected, amino acid-derived thioethers.
Donner
p. 1223 - 1226
(2007/10/02)

A convenient synthesis of chiral N-Boc-amino ethers as potential peptide bond surrogate units
Boron triflouride etherate and zinc triflate have been found to be effective catalysists for the synthetic route to chiral N-Boc-amino ethers via a Lewis acid-catalyzed ring-opening of N-acyl aziridines, derived from chiral amino acids.
Ho, Mengfei,Chung, James K. K.,Tang, Nancy
p. 6513 - 6516
(2007/10/02)

A Convenient One-Pot Conversion of N-Protected Amino Acids and Peptides into Alcohols
N-Protected amino acids and peptides are converted to alcohols by chemoselective reduction of their corresponding mixed anhydrides with sodium borohydride in tetrahydrofuran with dropwise addition of methanol.
Kokotos, George
p. 299 - 301
(2007/10/02)

Syntheses and Properties of Optically Active 2-Substituted Taurines
The synthesis of nine 2-substituted taurines (5a-i), including the marine natural product D-cysteinolic acid (5f), are described.These involve the successive conversion of N-t-butoxycarbonyl(Boc)-protected amino acid esters (1) into the N-Boc-2-aminoethanols (2), their O-mesylated derivatives (3), the deprotected 2-aminoethyl methanesulphonates (4), followed by the replacement of the mesyloxy group by a sulpho group to give the optically active taurines (5a-e,g-i).Hydrogenolysis of 2-benzyloxymethyltaurine (5e) gives D-cysteinolic acid (5f).The structure of another of the products, (5b), is also confirmed by an alternative synthesis from N-Boc-valine methyl ester (1b) via twoβ-bromoethylamine derivatives, (6b) and (7b).
Higashiura, Kunihiko,Morino, Hiroe,Matsuura, Hirohide,Toyomaki, Yoshio,Ienaga, Kazuharu
p. 1479 - 1481
(2007/10/02)