| dc.contributor.author |
Constantinou-Kokotou, V |
en |
| dc.contributor.author |
Couladouros, EA |
en |
| dc.contributor.author |
Georgiadis, MP |
en |
| dc.contributor.author |
Kokotos, G |
en |
| dc.contributor.author |
Georgiadis, TM |
en |
| dc.date.accessioned |
2014-06-06T06:41:58Z |
|
| dc.date.available |
2014-06-06T06:41:58Z |
|
| dc.date.issued |
1991 |
en |
| dc.identifier.issn |
00086215 |
en |
| dc.identifier.uri |
http://dx.doi.org/10.1016/0008-6215(91)89015-8 |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/359 |
|
| dc.subject.other |
Drug Products - Antibiotics |
en |
| dc.subject.other |
Alanine |
en |
| dc.subject.other |
Azido Group |
en |
| dc.subject.other |
Prumycin |
en |
| dc.subject.other |
Carbohydrates |
en |
| dc.subject.other |
3 deoxyprumycin |
en |
| dc.subject.other |
antibiotic agent |
en |
| dc.subject.other |
sugar |
en |
| dc.subject.other |
unclassified drug |
en |
| dc.subject.other |
antifungal activity |
en |
| dc.subject.other |
article |
en |
| dc.subject.other |
drug structure |
en |
| dc.subject.other |
drug synthesis |
en |
| dc.subject.other |
nuclear magnetic resonance |
en |
| dc.title |
Total synthesis of 4-(D-alanylamino)-2-amino-2,3,4-trideoxy-DL-threo-pentose (3-deoxy-DL-prumycin) |
en |
| heal.type |
journalArticle |
en |
| heal.identifier.primary |
10.1016/0008-6215(91)89015-8 |
en |
| heal.publicationDate |
1991 |
en |
| heal.abstract |
3-Deoxy-DL-prumycin (1) was synthesized from 2-furanmethanol (2-furfuryl alcohol, 2) in eleven steps in 15% total yield. Michael addition of azide anion to 2,3-dideoxy-DL-pent-2-enopyranos-4-ulose (3) and reduction in situ of the adduct afforded the key intermediates 5 and 6. Introduction of a second azido group with inversion of configuration at C-4 afforded intermediates 14 and 17, both of wich had a threo configuration in regard to C-2 and C-4. Coupling with D-alanine and total deprotection yielded the title compound 1.3-Deoxy-DL-prumycin (1) was synthesized from 2-furanmethanol (2-furfuryl alcohol, 2) in eleven steps in 15% total yield. Michael addition of azide anion to 2,3-dideoxy-DL-pent-2-enopyranos-4-ulose (3) and reduction in situ of the adduct afforded the key intermediates 5 and 6. Introduction of a second azido group with inversion of configuration at C-4 afforded intermediates 14 and 17, both of which had a threo configuration in regard to C-2 and C-4. Coupling with D-alanine and total deprotection yielded the title compound 1. |
en |
| heal.journalName |
Carbohydrate Research |
en |
| dc.identifier.volume |
222 |
en |
| dc.identifier.doi |
10.1016/0008-6215(91)89015-8 |
en |
| dc.identifier.spage |
163 |
en |
| dc.identifier.epage |
172 |
en |