| dc.contributor.author |
CONSTANTINOUKOKOTOU, 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 |
2014-06-06T06:41:59Z |
|
| dc.date.available |
2014-06-06T06:41:59Z |
|
| dc.date.issued |
1991 |
en |
| dc.identifier.issn |
0008-6215 |
en |
| dc.identifier.uri |
http://62.217.125.90/xmlui/handle/123456789/365 |
|
| dc.subject.classification |
Biochemistry & Molecular Biology |
en |
| dc.subject.classification |
Chemistry, Applied |
en |
| dc.subject.classification |
Chemistry, Organic |
en |
| dc.subject.other |
PRUMYCIN |
en |
| dc.title |
PRODUCTS FROM FURANS .11. 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.language |
English |
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 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.publisher |
ELSEVIER SCIENCE BV |
en |
| heal.journalName |
CARBOHYDRATE RESEARCH |
en |
| dc.identifier.volume |
222 |
en |
| dc.identifier.isi |
ISI:A1991GZ50700015 |
en |
| dc.identifier.spage |
163 |
en |
| dc.identifier.epage |
172 |
en |