Product Details of 123-11-5. Recently I am researching about C-GLYCOSYLIDENE DERIVATIVES; RAMBERG-BACKLUND REACTION; PROTECTED SUGAR LACTONES; EFFICIENT SYNTHESIS; ENOL ETHERS; STEREOCONTROLLED SYNTHESIS; DEHYDROQUINATE SYNTHASE; CONVENIENT SYNTHESIS; SUBSTRATE-ANALOGS; FACILE SYNTHESIS, Saw an article supported by the JST CREST Grant, Japan [JPMJCR18S1]; Koshiyama Research Grant. Published in AMER CHEMICAL SOC in WASHINGTON ,Authors: Oka, N; Mori, A; Suzuki, K; Ando, K. The CAS is 123-11-5. Through research, I have a further understanding and discovery of 4-Methoxybenzaldehyde
One-pot Julia olefination using ribofuranosyl sulfones is described. The alpha-anomers of the ribofuranosyl sulfones were synthesized with complete alpha-selectivity via the glycosylation of heteroarylthiols using ribofuranosyl iodides as glycosyl donors and the subsequent oxidation of the resulting heteroaryl 1-thioribofuranosides with magnesium monoperphthalate (MMPP). The Julia olefination of the alpha-ribofuranosyl sulfones with aldehydes proceeded smoothly in one pot to afford the thermodynamically less stable (E)-exo-glycals with modest-to-excellent stereoselectivity (up to E/Z = 94:6) under the optimized conditions. The E selectivity was especially high for aromatic aldehydes. In contrast, the (Z)-exo-glycal was obtained as the main product with low stereoselectivity when the corresponding beta-ribofuranosyl sulfone was used (E/Z = 41:59). The remarkable impact of the anomeric configuration of the ribofuranosyl sulfones on the stereoselectivity of the Julia olefination has been rationalized using density functional theory (DFT) calculations. The protected ribose moiety of the resulting exo-glycals induced completely a-selective cyclopropanation on the exocyclic carbon-carbon double bond via the Simmons-Smith-Furukawa reaction. The 2-cyanoethyl group was found to be useful for the protection of the exo-glycals, as it could be removed without affecting the exocyclic C=C bond.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles