Topic
Glycal
About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.
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TL;DR: Anti-HIV studies demonstrated that these 4'-thio nucleosides were less cytotoxic to T-lymphocyte (i.e. MT-4 cells) than the corresponding 4'-ethynyl derivatives of 2'-deoxycytidine (44), 2-deoxyadenosine (45) and 2'deoxyguanosine (46).
Abstract: The synthesis of 4′-ethynyl-2′-deoxy-4′-thioribonucleosides was carried out utilizing an electrophilic glycosidation in which 4-ethynyl-4-thiofuranoid glycal 16 served as a glycosyl donor. Electrophilic glycosidation between 16 and the silylated nucleobases (N4-acetylcytosine, N6-benzoyladenine, and N2-acetyl-O6-diphenylcarbamoylguanine) was carried out in the presence of N-iodosuccinimide (NIS), leading to the exclusive formation of the desired β-anomers 29, 33, and 36. Anti-HIV studies demonstrated that these 4′-thio nucleosides were less cytotoxic to T-lymphocyte (i.e., MT-4 cells) than the corresponding 4′-ethynyl derivatives of 2′-deoxycytidine (44), 2′-deoxyadenosine (45), and 2′-deoxyguanosine (46). Comparison of the selectivity indices (SI) was made between 4′-thionucleosides (32, 41, and 43) and the corresponding 4′-oxygen analogues 44-46 by using the reported CC50 and EC50 values. In the case of cytosine and adenine nucleosides, comparable SI values were obtained as follows: 32 (545) and 44 (458...
15 citations
TL;DR: A novel metal-free strategy for a rapid and α-selctive C-alkynylation of glycals was developed that can access C-glycosides in a single step from a variety of acetylenes, i.e., arylacetylenes and most importantly aliphatic alkynes.
Abstract: A novel metal-free strategy for a rapid and α-selctive C-alkynylation of glycals was developed. The reaction utilizes TMSOTf as a promoter to generate in situ trimethylsilylacetylene for C-alkynylation. Thanks to this methodology, we can access C-glycosides in a single step from a variety of acetylenes , i.e., arylacetylenes and most importantly aliphatic alkynes.
15 citations
TL;DR: The syntheses reported here will allow for ready access to novel ring expanded carbohydrate analogs and moderate diastereoselectivity was observed for the reduction based on the starting oxepinone.
15 citations
TL;DR: The key step of this synthesis is an application of the known Claisen thermal rearrangement of a glucal derivative, the vinyl allyl ether (+)-3b, which allows to switch the glycal structure into the corresponding carba analog scaffold.
15 citations
TL;DR: The 3-thio-glycals were successfully employed for the synthesis of 3′-mercapto-3′-deamino-doxorubicin and its analogues as mentioned in this paper.
15 citations