36016-38-3Relevant articles and documents
High-throughput protein glycomics: Combined use of chemoselective glycoblotting and MALDI-TOF/TOF mass spectrometry
Nishimura, Shin-Ichiro,Niikura, Kenichi,Kurogochi, Masaki,Matsushita, Takahiko,Fumoto, Masataka,Hinou, Hiroshi,Kamitani, Ryousuke,Nakagawa, Hiroaki,Deguchi, Kisaburo,Miura, Nobuaki,Monde, Kenji,Kondo, Hirosato
, p. 91 - 96 (2005)
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Enantioselective Diels-Alder reaction with an α-chloronitroso dienophile derived from 5-O-acetyl-2,3-isopropylidenedioxy-D-ribose
Defoin,Joubert,Heuchel,Strehler,Streith
, p. 1719 - 1726 (2000)
Crystalline 5-O-acetyl-2,3-isopropylidenedioxy-D-ribonolactone oxime (8) was synthesised from D-ribose in 40% overall yield. The chloronitroso dienophile 3b was obtained from 8 by oxidation with t-BuOCl and underwent asymmetric Diels-Alder reaction with cyclic and acyclic dienes 10-13 to give crystalline adducts 14a-17a in good yield and excellent enantiomeric excess (93-99%).
Palladium-Catalyzed C-O Cross-Coupling as a Replacement for a Mitsunobu Reaction in the Development of an Androgen Receptor Antagonist
Hager, Anastasia,Guimond, Nicolas,Grunenberg, Lars,Hanisch, Christine,Steiger, Sebastian,Preuss, Andre
, p. 654 - 660 (2021/03/15)
A scalable and efficient synthesis of N-{trans-4-[(8-cyanoquinolin-4-yl)oxy]cyclohexyl}-3-fluorobenzamide (BAY 1161116), an androgen receptor antagonist, is reported. The original synthesis included a low-yielding Mitsunobu reaction and employed cis-aminocyclohexanol, which is accessible only via a troublesome synthesis, as a key building block. The novel synthetic pathway starts from readily available trans-aminocyclohexanol and features a palladium-catalyzed etherification reaction in place of the Mitsunobu reaction as the key step. This four-step synthesis can be performed reliably on a multikilogram scale, and purification of all intermediates as well as the final product can be achieved by simple extraction and crystallization procedures.
Photo-auxiliary approach to control excited state reactivity: Cross [2+2]-photocycloaddition of oxazolidinone based hydrazides
Ahuja, Sapna,Iyer, Akila,Kandappa, Sunil Kumar,Sivaguru, Jayaraman
, (2019/07/31)
Chiral oxazolidinone based hydrazides undergo efficient cross [2 + 2]-photocycloaddition upon visible light illumination. Oxazolidinone functionality acted as an energy harvesting photo-auxiliary. The cross [2 + 2]-photocycloaddition proceeded efficiently from the excited state with moderate to excellent isolated yield of the photoproduct. The photo-auxiliary can be conveniently removed post-photoreaction, which highlights the versatility of this strategy.
FMOC PROTECTED (2S)-2-AMINO-8-[(1,1-DIMETHYLETHOXY)AMINO]-8-OXO-OCTANOIC ACID, (S)-2-AMINO-8-OXONONANOIC ACID AND (S)-2-AMINO-8-OXODECANOIC ACID FOR PEPTIDE SYNTHESIS
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Page/Page column 42-43, (2019/12/04)
The invention discloses Fmoc protected (2S)-2-amino-8-[(1,1- dimethylethoxy)amino]-8-oxo-octanoic acid, (S)-2-amino-8- oxononanoic acid and (S)-2-amino-8-oxodecanoic acid for use in peptide synthesis, such as solid phase synthesis, as well as the peptide H3K27 (Ac-Lys-Ala-Ala-Arg-Aox-Ser-Ala-NH2) prepared from Fmoc protected (2S)-2-amino-8-[(1,1-dimethylethoxy)amino]-8-oxo-octanoic acid (Aox). These three exemplary compounds as well as their unprotected forms are claimed in the form of four generic formulae. The first of these four formulae is (formula (I)) where -NPro is a protected amino group, such as an amino group protected with a base-labile protecting group, -L- is alkylene, heteroalkylene, arylene or aralkylene, -X- is a covalent bond, -N(H) - or -N(RN)-, where -RN is alkyl, -R2 is hydrogen or alkyl, -R3 is alkyl, such as C2-10 alkyl, or heterocyclyl, and -LAA- and -R1 are as defined in the claims.
