Academic Journal
A Novel Glycosyl Donor with a Triisopropylsilyl Nonparticipating Group in Benzyl-Free Stereoselective 1,2-cis-Galactosylation
| Title: | A Novel Glycosyl Donor with a Triisopropylsilyl Nonparticipating Group in Benzyl-Free Stereoselective 1,2-cis-Galactosylation |
|---|---|
| Authors: | Leonid O. Kononov, Alexander I. Zinin, Nelly N. Malysheva, Alexander O. Chizhov, Vladimir I. Torgov, Polina I. Abronina, Elena V. Stepanova |
| Source: | Synlett |
| Publisher Information: | Georg Thieme Verlag KG, 2017. |
| Publication Year: | 2017 |
| Subject Terms: | conformation, стереоселективный синтез, стереоселективность, glycosylation, triisopropylsilyl group, 4-(3-chloropropoxy)phenyl glycosides, защитные группы, конформация, stereoselectivity, 01 natural sciences, фенилгликозиды, 3. Good health, 0104 chemical sciences, гликозилирование, protecting groups, stereoselective synthesis |
| Description: | A novel glycosyl donor with a triisopropylsilyl (TIPS) nonparticipating group at O-2 is introduced for use in 1,2-cis-galactosylation. Coupling the 2-O-TIPS-substituted thiogalactoside donor with a series of mono- and disaccharide glycosyl acceptors was found to lead exclusively to α-linked oligosaccharides. The observed exceptionally high α-selectivity was interpreted in terms of conformational changes in the glycosyl cation induced by the bulky 2-O-TIPS group. |
| Document Type: | Article |
| File Description: | application/pdf |
| Language: | English |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/s-0036-1589028 |
| Access URL: | http://earchive.tpu.ru/bitstream/11683/64909/1/reprint-nw-22798.pdf https://www.thieme-connect.de/products/ejournals/html/10.1055/s-0036-1589028 https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1589028 https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0036-1589028 https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-0036-1589028.pdf http://earchive.tpu.ru/handle/11683/64909 |
| Rights: | CC BY NC |
| Accession Number: | edsair.doi.dedup.....6df1f0e1d828c13e419971d30ddb857a |
| Database: | OpenAIRE |
Be the first to leave a comment!