Synonyms:SR-05000001559;BSPBio_002408;SCHEMBL267918;HMS2092M12;Pharmakon1600-01500838;CCG-38845;NSC757799;NSC-757799;SBI-0052082.P002;AB00052595_02;SR-05000001559-1;SR-05000001559-2;SR-05000001559-3;SR-05000001559-4
99%min *data from raw suppliers
Vitamin D3 *data from reagent suppliers
T+,
T
There total 141 articles about Pharmakon1600-01500838 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
Reference yield: 74.0%
Reference yield: 19.2%
Reference yield: 19.2%
The research focuses on the enantioselective synthesis of a key A-ring intermediate, specifically the R,β-unsaturated aldehyde 1, which is crucial for the preparation of 1α,25-dihydroxyvitamin D3 (calcitriol). The purpose of this study is to develop a novel and efficient approach to synthesize this intermediate, starting from the inexpensive material (R)-carvone, with the potential to create vitamin D3 analogues with modifications at the C-2 position. The research concludes that a new strategy has been successfully developed, which involves 11 steps and yields the desired intermediate in 24% overall yield, with the ene reaction as the key step. This method could be applied to synthesize vitamin D3 analogues with modifications at the C-2 position, which may have increased binding affinity for the vitamin D receptor (VDR) and potent agonistic activity. Key chemicals used in the process include (R)-carvone, LAH, m-CPBA, nitrobenzoate, MOM group, Zn powder, NaI, and active forms of formaldehyde, among others.
The research describes a regio- and stereoselective ruthenium-catalyzed hydrovinylation of 1,3-dienes, which is a C-C bond-forming reaction that uses ethylene as a cheap feedstock and proceeds in an atom-economical manner. The study focuses on the addition of ethylene to 1,3-dienes and 1-vinylcycloalkenes, catalyzed by two ruthenium complexes, resulting in the formation of 3-methyl-1,4-dienes. The reaction is particularly significant for a steroidal-based 1-vinylcycloalkene, as it yields a product with a 20(S) configuration, which is the opposite of most naturally occurring steroids. The chemicals used in the process include ethylene, 1,3-dienes, 1-vinylcycloalkenes, and two ruthenium catalysts, which are crucial for the selective addition reaction. The study concludes that this hydrovinylation reaction has potential for synthetic applications, especially in generating side chains with the 20(S) configuration, which is valuable for the preparation of nonnatural vitamin D3 analogues and other pharmaceutically relevant compounds.
The study investigates the lithium dimethylcuprate induced conversion of propargylic esters into allenes, using a steroidal C/D fragment derived from vitamin D3 as a stereochemical probe. The researchers reacted (CH3)2CuLi with various C-8 propargylic esters derived from Grundmann's ketone, a C/D steroidal fragment originating from vitamin D3, to produce corresponding allenes. The stereocheristry of the resulting allenes indicated a preferred anti 1,3-substitution mode. The study used the C/D ring fragment from Grundmann's ketone as a convenient stereochemical probe for this conversion. The propargylic esters were prepared from Grundmann's ketone through a series of reactions involving tert-BuLi, Ph2Se2, MCPBA oxidation, and hydrolysis. The resulting allenes' stereocheristry was determined by comparing their 'H-NMR spectral data with those of the product of a reaction sequence involving propargylic alcohol and PhSCl. The study concludes that the predominant product in the organocopper promoted conversion of propargylic esters into allenes originates from an anti mode of displacement, regardless of the nature of the leaving group.
The study investigates the synthesis and biological properties of novel D-ring analogues of 1a,25-dihydroxyvitamin D3 (calcitriol). The researchers aimed to develop analogues that can dissociate cell-differentiating effects from calcemic effects, focusing on 17-methyl D-ring analogues lacking the six-membered C-ring. The synthesis involved the Lythgoe coupling of an 8-formyl-D-ring fragment with phosphine oxides, leading to the creation of analogues with both natural (R) and unnatural (S) configurations at C-20. The study evaluated the affinity of these analogues to the vitamin D receptor (VDR) and their antiproliferative activities in various cell lines, finding that some analogues, particularly the hexafluoro analogues, displayed high antiproliferative activity and significant differentiation between antiproliferative and calcemic effects. The chemicals involved included 1a,25-dihydroxyvitamin D3, various phosphine oxides, and a series of ketones used in the synthesis process.
The study investigates the design and total convergent synthesis of new analogs of cholecalciferol (vitamin D) with the CD-ring system replaced by a two-carbon aliphatic spacer. The researchers aimed to simplify the structure of vitamin D-based therapeutics by identifying the essential structural parts responsible for its activity. The key chemicals involved include vitamin D derivatives, such as vitamin D3 and 1α-hydroxyvitamin D3, which serve as precursors for the ring fragments. The chain fragment is derived from S-(-)-β-citronellol, a natural monoterpene. The synthesized compounds, RAD and RAD2, are designed as des-CD analogs of 25-OH-D3 and 1,25-(OH)2D3, respectively, with an unnatural configuration at C-20. The study employs various reagents and conditions, such as imidazole, t-BuMe2SiCl, MCPBA, lithium triethylborohydride, and pyridinium chlorochromate, to achieve the desired modifications and coupling of the ring and chain fragments. The results provide insights into the potential for developing more effective therapeutic agents based on the simplified structure of vitamin D.
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