Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-l-glycero-α-d-manno-heptopyranose.
| cam.issuedOnline | 2015-03-10 | |
| dc.contributor.author | Stanetty, Christian | |
| dc.contributor.author | Baxendale, Ian R | |
| dc.contributor.orcid | Baxendale, Ian R [0000-0003-1297-1552] | |
| dc.date.accessioned | 2018-12-20T00:31:14Z | |
| dc.date.available | 2018-12-20T00:31:14Z | |
| dc.date.issued | 2015-04 | |
| dc.description.abstract | The higher-carbon sugar l-glycero-d-manno-heptose is a major constituent of the inner core region of the lipopolysaccharide (LPS) of many Gram-negative bacteria. All preparative routes used to date require multiple steps, and scalability has been rarely addressed. Here a highly practical synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-l-glycero-α-d-manno-heptopyranose by a simple four-step sequence starting from l-lyxose is disclosed. Only two recrystallisations are required and the process was demonstrated on a >100 mmol scale, yielding 41 g of the target compound. | |
| dc.format.medium | Print-Electronic | |
| dc.identifier.doi | 10.17863/CAM.34546 | |
| dc.identifier.eissn | 1099-0690 | |
| dc.identifier.issn | 1434-193X | |
| dc.identifier.uri | https://www.repository.cam.ac.uk/handle/1810/287239 | |
| dc.language | eng | |
| dc.language.iso | eng | |
| dc.publisher | Wiley | |
| dc.publisher.url | http://dx.doi.org/10.1002/ejoc.201500024 | |
| dc.rights | Attribution 4.0 International | |
| dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | |
| dc.subject | Allylation | |
| dc.subject | Carbohydrates | |
| dc.subject | Indium | |
| dc.subject | Rare sugars | |
| dc.subject | Synthetic methods | |
| dc.title | Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-l-glycero-α-d-manno-heptopyranose. | |
| dc.type | Article | |
| prism.endingPage | 2726 | |
| prism.issueIdentifier | 12 | |
| prism.publicationDate | 2015 | |
| prism.publicationName | European J Org Chem | |
| prism.startingPage | 2718 | |
| prism.volume | 2015 | |
| rioxxterms.licenseref.startdate | 2015-04 | |
| rioxxterms.licenseref.uri | http://www.rioxx.net/licenses/all-rights-reserved | |
| rioxxterms.type | Journal Article/Review | |
| rioxxterms.version | VoR | |
| rioxxterms.versionofrecord | 10.1002/ejoc.201500024 |
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