203508-62-7Relevant articles and documents
Stereoselective Palladium-Catalyzed Approach to Vitamin D3 Derivatives in Protic Medium
Carballa, Diego,Sigüeiro, Rita,Rodríguez-Docampo, Zaida,Zacconi, Flavia,Maestro, Miguel A.,Mouri?o, Antonio
, p. 3314 - 3320 (2018/02/12)
We describe an efficient convergent synthesis of vitamin D3 metabolites and analogues. The synthetic strategy relies on a tandem Pd-catalyzed A-ring closure and Suzuki–Miyaura coupling to the CD-side chain component to set directly the vitamin D triene system under protic conditions. This strategy enables rapid access to vitamin D3 and 3-epi-vitamin D3 metabolites and analogues modified at the side chain for biological evaluation and structural and metabolic studies.
SOLID FORMS OF 2-(TERT-BUTYLAMINO)-4-((1R,3R,4R)-3-HYDROXY-4-METHYLCYCLOHEXYLAMINO)-PYRIMIDINE-5-CARBOXAMIDE, COMPOSITIONS THEREOF AND METHODS OF THEIR USE
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Paragraph 0649; 0650, (2015/08/04)
Provided herein are formulations, processes, solid forms and methods of use relating to 2-(tert-butylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide.
SOLID FORMS OF 2-(TERT-BUTYLAMINO)-4-((1R,3R,4R)-3-HYDROXY-4-METHYLCYCLOHEXYLAMINO)-PYRIMIDINE-5-CARBOXAMIDE, COMPOSITIONS THEREOF AND METHODS OF THEIR USE
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Paragraph 00452, (2015/11/02)
Provided herein are formulations, processes, solid forms and methods of use relating to 2- (tert-butylamino)-4-((lR,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5- carboxamide.
Vitamin D: A concise synthesis of the C19 hydroxylated enyne A-ring, an interesting precursor for the preparation of C19 substituted vitamin D analogues
Rodriguez, Rapha?l,Ollivier, Cyril,Santelli, Maurice
, p. 2289 - 2292 (2007/10/03)
A new C19 hydroxylated enyne 15, as potential A-ring building block of vitamin D analogues, was synthesized in enantiomerically pure form in nine steps from (-)-(S)-limonene. This short synthesis involved ozonolyzis of 1,2-limonene oxide followed by a Criegee rearrangement, epoxide trans diaxial ring opening by lithium acetylide, elimination, epoxidation and syn β-elimination of the resulting homopropargylic oxirane.
Synthesis and absolute configuration of rotundial, a mosquito repellent from the leaves of vitex rotundiforia
Takikawa, Hirosato,Yamazaki, Yuichiro,Mori, Kenji
, p. 229 - 232 (2007/10/03)
The enantiomers of rotundial (1), a mosquito repellent from the leaves of Vitex rotundiforia, were synthesized from the enantiomers of limonene oxide (2). The absolute configuration of natural rotundial was determined to be R.
Trichodiene Synthase. Synergistic Inhibition by Inorganic Pyrophosphate and Aza Analogs of the Bisabolyl Cation
Cane, David E.,Yang, Guohan,Coates, Robert M.,Pyun, Hyung-Jung,Hohn, Thomas M.
, p. 3454 - 3462 (2007/10/02)
A series of aza analogs of the bisabolyl and α-terpinyl cations were tested as inhibitors of the sesquiterpene cyclase, trichodiene synthase.Both (R)- and (S)-16 and (R)- and (S)-13 as well as trimethylamine were only weak inhibitors when incubated alone.In the presence of inorganic pyrophosphate, itself a known competitive inhibitor of trichodiene synthase, all five amines showed strong cooperative competitive inhibition with an enhancement factor estimated to be 10-40.The apparent induced inhibition constant αKJ decreased in going from trimethylamine to the monoterpene analogs 13 and was strongest for the sesquiterpene analogs 16, indicating that both electrostatic and hydrophobic interactions are important in the binding of each intermediate analog.The cyclase showed little discrimination, however, between the individual enantiomers of each inhibitor.
