86884-87-9Relevant academic research and scientific papers
4,6-SUBSTITUTED-PYRAZOLO[1,5-a]PYRAZINES AS JANUS KINASE INHIBITORS
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Paragraph 00383, (2016/06/28)
Compounds of Formula I: and stereoisomers and pharmaceutically acceptable salts and solvates thereof in which R1, R2, R3 and R4 have the meanings given in the specification, are inhibitors of one or more JAK kinases and are useful in the treatment of JAK kinase-associated diseases and disorders, such as autoimmune diseases, inflammatory diseases, rejection of transplanted organs, tissues and cells, as well as hematologic disorders and malignancies and their co-morbidities.
Chemoenzymatic enantioselective synthesis of 2-substituted glycerol derivatives
Bolduc, Melanie,Bergeron, Jerome,Michaud, Annie,Pelchat, Nicholas,Morin, Pierre,Dasser, Mohammed,Chenevert, Robert
experimental part, p. 428 - 433 (2012/07/28)
2-Substituted glycerol derivatives 4a-g were resolved by acylation with vinyl butyrate in the presence of lipases in organic media. The reverse reaction, the enzymatic hydrolysis of the corresponding butyrates 5a-g, was also highly stereoselective and pro
Development of a multikilogram synthesis of a chiral epoxide precursor to a CCR1 antagonist. Use of in situ monitoring for informed optimisation via fragile intermediates
Ange, Debra,Booker, James E. M.,Pedge, Nicholas,Sinclair, Rhona,Sleigh, Chris,Stefinovic, Marijan,Vaz, Luis-Manuel,Way, Edward
experimental part, p. 72 - 84 (2010/05/02)
The optimisation and scale up of a manufacturing route to a key intermediate, acetic acid 4-acetylamino-3-(2-methyl-oxiranyl- methoxy)phenyl ester (2), utilising a SNAr coupling, the hydro- genation of a nitro moiety and the conversion of a chi
USE OF INTERMEDIATES ((R ) -2,2, 4-TRIMETHYL-L, 3-DIOXOLANE-4-YL) METHANOL (A), 3-F LUORO-4-NITRO-PHENOL (B) AND 1- (4-CHLORO- BENZYL) -PIPERIDIN-4-YLAMINE (C)
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Page/Page column 4; 13-14, (2009/04/25)
The present invention relates to novel processes for the preparation of intermediate compounds which can be used to prepare therapeutic agents. The present invention also relates to novel intermediate compounds which can be used to prepare therapeutic agents. More specifically, the invention relates to the use of intermediates ((R) -2,2,4-trimethyl-l, 3- dioxolane-4 -yl) methanol (A), 3-f luoro-4-nitro-phenol (B) and 1- (4-chloro-benZyl) -piperidin-4-ylamine (C).
Facile synthesis of C2-symmetric chiral crown ethers with two reactive hydroxymethyl groups
Nakatsuji, Yohji,Nakahara, Yoshio,Nagamiya, Katsumori,Itoh, Yuki,Uesugi, Kentaro,Ishida, Naohisa,Muraoka, Masahiro,Kida, Toshiyuki,Akashi, Mitsuru
, p. 2973 - 2978 (2008/03/13)
Two C2-symmetric chiral crown ethers, (2S,12S)-2,12- bis(hydroxymethyl)-2,12-dimethyl-18-crown-6 and (2R,9R)-2,9-bis(hydroxymethyl)- 2,9-dimethyl-18-crown-6 were synthesized from a chiral subunit, [(45)-2,2,4-trirnethyl-1,3-dioxolane-4-yl]methanol, at high enantiomeric purity over several steps. This synthetic method offers the potential to construct a variety of C2-symmetric chiral crown ethers using diverse combinations of building blocks. Georg Thieme Verlag Stuttgart.
Facile Chemoenzymatic Preparation of Enantiomerically Pure 2-Methylglycerol Derivatives as Versatile Trifunctional C4-Synthons
Wirz, Beat,Barner, Richard,Huebscher, Joseph
, p. 3980 - 3984 (2007/10/02)
Both enantiomers of a series of synthetically valuable 2-methylglycerol derivatives have been prepared with >99percent ee using a chemoenzymatic reaction sequence.The introduction of chirality was achieved by enantioselective esterification of 1,2-O-protected 2-methylglycerol 3 or enantioselective hydrolysis of its butyryl ester 4.The enzymatic reaction proceeded with unusually high selectivity and velocity for a primary alcohol (ester) substrate.
BRANCHED-CHAIN DERIVATIVES OF ACYCLIC ADENOSINE ANALOGS: ALKYL AND HYDROXYMETHYL DERIVATIVES OF S-ADENOSYL-L-HOMOCYSTEINASE INHIBITORS SUBSTITUTED AT THE 2- AND 3-POSITION OF THE SIDE CHAIN
Holy, Antonin
, p. 248 - 265 (2007/10/02)
Reaction of 1,3-dichloro-2-propanone (VII) with methylmagnesium chloride, followed by alkaline hydrolysis, afforded 2-methylpropane-1,2,3-triol (VIII) which on treatment with 2,2-dimethoxypropane and subsequent tosylation give 4-(p-toluenesulfonyloxymethyl)-2,2,4-trimethyl-1,3-dioxolane (IXb).Compound IXb was condensed with sodium salt of adenine and the intermediate X was acid-hydrolysed to give 9-(RS)-(2,3-dihydroxy-2-methylpropyl)adenine (XI).Oxidation of XI with sodium periodate led to 9-(2-oxopropyl)adenine (XII). 9-(RS)-(2-Hydroxy-2-hydroxymethyloctyl)adenine (XVI) was obtained analogously from compound VII and hexylmagnesium bromida via triol XIV.Methyl 2-bromomethyl-2-propenoate (XVII) reacted with sodium salt of adenine and the resulting methyl 2-(adenin-9-ylmethyl)-2-propenoate (XVIII) was hydroxylated with sodium perchlorate and osmium tetroxide.The obtained methyl (RS)-2-(adenin-9-ylmethyl)-2,3-dihydroxypropanoate (XIX) was alkali-hydrolysed to give sodium salt of the acid XX.Reduction of ester XIX with sodium borohydride furnished 9-(RS)-(2,3-dihydroxy-2-hydroxymethylpropyl)adenine (XXI). 1-Nonen-3-ol (XXIII), obtained by reaction of propenal with hexylmagnesium bromide, was converted by hydroxylation with osmium tetroxide into nonane-1,2,3-triol (XXIVa) and further into its 1-O-p-toluenesulfonate XXIVb which reacted with 2,2-dimethoxypropane to give 2,2-dimethyl-4-hexyl-5-(p-toluenesulfonyloxymethyl)-1,3-dioxolane (XXV).Compound XXV reacted with adenine and the resulting intermediate XXVI was converted into 9-(RS)-(2,3-dihydroxynonyl)adenine (XXVII) by acid hydrolysis. 9-(3-Methyl-2-buten-1-yl)adenine (XXVIII), obtained by alkylation of sodium salt of adenine with 1-bromo-3-methyl-2-butene, was oxidized with potassium permanganate in an acid medium to give 9-(3-hydroxy-2-oxo-3-methylbutyl)adenine (XXIX).This compound was converted into 9-(RS)-(2,3-dihydroxy-3-methylbutyl)adenine (XXX) by reduction with sodium borohydride. 4-C-Hydroxymethyl-1,2-O-isopropylidene-α-D-xylofuranose (XXXII) reacted with 2,2-dimethoxypropane under formation of 4-C-hydroxymethyl-1,2:3,5-di-O-isopropylidene derivative XXXIIIa whose p-toluenesulfonyl derivative XXXIIIb on treatment with adenine afforded 4-C-(adenin-9-yl)methyl-1,2:3,5-di-O-isopropylidene-α-D-xylofuranose (XXXIV).Acid hydrolysis of this compound, followed by oxidation in an alkaline medium, gave (2S,3R)-4-(adenin-9-yl)-3-hydroxymethyl-2,3-dihydroxybutanoic acid, isolated as its ethyl ester XXXVI.
Trihydric alcohol derivatives
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, (2008/06/13)
Certain novel trihydric alcohol derivatives, useful as herbicides and fungicides.
