Tricyclic furanoid dichloroacetyl orthoesters of D-mannose from 1,2-O-trichloroethylidene-ß-D-mannofuranose
Küçük Resim Yok
Tarih
2004
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
1,2-O-(R)-Trichloroethylidene-ß-D-mannofuranose (1) was obtained from the reaction of D-mannose with chloral. Reaction of 1 with potassium tert-butoxide (3Mequiv) gave the thermodynamically stable 1,2,5-O- orthodichloroacetyl-ß-D-mannofuranose as the sole product whereas 1.5Mequiv of reagent gave the kinetically controlled 1,2,3-O-orthodichloroacetyl-ß- D-mannofuranose (10) as the main product. Orthoester 10 gave the 5,6-isopropylidene derivative, which was also obtained from the reaction of 5,6-O-isopropylidene-1,2-O-(R)-trichloroethylidene-ß-D-mannofuranose with potassium tert-butoxide (1.5Mequiv). These novel orthoesters are expected to prove useful as protecting groups and as building blocks in the formations of new mannofuranisidic units. © 2004 Elsevier Ltd. All rights reserved.
Açıklama
Anahtar Kelimeler
Glycosylation, Sugar acetals, Sugar orthoesters, Trichloroethylidene acetals
Kaynak
Carbohydrate Research
WoS Q Değeri
Scopus Q Değeri
Q2
Cilt
339
Sayı
10
