A further investigation of the stannic chloride-catalyzed condensation reaction of 1-hexene and 1,2,3,5-tetra-O-acyl-[beta]--ribofuranoses
dc.contributor.author | Cupps, Thomas L. | en_US |
dc.contributor.author | Wise, Dean S. | en_US |
dc.contributor.author | Townsend, Leroy B. | en_US |
dc.date.accessioned | 2006-04-07T18:43:19Z | |
dc.date.available | 2006-04-07T18:43:19Z | |
dc.date.issued | 1983-04-16 | en_US |
dc.identifier.citation | Cupps, Thomas L., Wise, Dean S., Townsend, Leroy B. (1983/04/16)."A further investigation of the stannic chloride-catalyzed condensation reaction of 1-hexene and 1,2,3,5-tetra-O-acyl-[beta]--ribofuranoses." Carbohydrate Research 115(): 59-73. <http://hdl.handle.net/2027.42/25238> | en_US |
dc.identifier.uri | http://www.sciencedirect.com/science/article/B6TFF-42NJH4S-R9/2/679a03d504e232a6d8c485cb6c2af031 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/25238 | |
dc.description.abstract | The reaction of 1-hexene with either 1-O-acetyl-2,3,5-tri-O-benzoyl-[beta]--ribofuranose (5b) or 1,2,3,5-tetra-O-acetyl-[beta]--ribofuranose (5a) in the presence of stannic chloride leads to the formation of a complex mixture of products. By a combination of 1H-n.m.r. and mass spectroscopy, the products were shown to be anomeric and diastereomeric mixtures of the 8,9,11-tri-O-acyl-protected derivatives of 7,10-anhydro-1,2,3,4,5,6-hexadeoxy--allo(altro)-undec-4-enitol (1) and 7,10-anhydro-5-chloro-1,2,3,4,5,6-hexadeoxy--allo(altro)-undecitol (2). The [alpha] anomer of 1 was the predominant anomer, whereas the [alpha] and [beta] anomers of 2 were present in approximately equal amounts. It was found that 2 was not formed when trimethylsilyl trifluoromethanesulfonate was used as the catalyst instead of stannic chloride. The acyl-protected sugar 3,6-anhydro-2-deoxy--allo(altro)-heptose (3), prepared by ozonolysis of 1, reacted with tert-butoxycarbonylmethyltriphenylphosphorane to give tert-butyl trans-5,8-anhydro-6,7,9-tri-O-acetyl-2,3,4-trideoxy--allo(altro)-non-2-enanate (4). The basicity of the ylide was sufficient to cause anomerization and resulted in an [alpha],[beta] ratio of 5:1 in the product, 4. | en_US |
dc.format.extent | 959325 bytes | |
dc.format.extent | 3118 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | Elsevier | en_US |
dc.title | A further investigation of the stannic chloride-catalyzed condensation reaction of 1-hexene and 1,2,3,5-tetra-O-acyl-[beta]--ribofuranoses | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Molecular, Cellular and Developmental Biology | en_US |
dc.subject.hlbsecondlevel | Materials Science and Engineering | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbsecondlevel | Biological Chemistry | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.subject.hlbtoplevel | Health Sciences | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109 U.S.A. | en_US |
dc.contributor.affiliationum | Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109 U.S.A. | en_US |
dc.contributor.affiliationum | Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109 U.S.A. | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/25238/1/0000680.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1016/0008-6215(83)88135-X | en_US |
dc.identifier.source | Carbohydrate Research | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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