1128-40-1Relevant articles and documents
Rapid access to rare natural pyranosides using 1,2-diacetal protected intermediates
Ley, Steven V.,Owen, Dafydd R.,Wesson, Kieron E.
, p. 2805 - 2806 (1997)
The synthesis of six rare methylpyranosides from common manno- and galacto-pyranoside starting materials has been achieved by the expedient use of 1,2-diacetal protecting group methodology highlighting its compatibility with a number of other common synthetic procedures.
Synthesis of β-(1→2)-Linked 6-Deoxy- l -altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor
Shen, Zhengnan,Mobarak, Hani,Li, Wei,Widmalm, G?ran,Yu, Biao
, p. 3062 - 3071 (2017/03/23)
The β-(1→2)-linked 6-deoxy-l-altropyranose di- to pentasaccharides 2-5, relevant to the O-antigen of the infectious Yersinia enterocolitica O:3, were synthesized for the first time. The challenging 1,2-cis-altropyranosyl linkage was assembled effectively via glycosylation with 2-O-benzyl-3,4-di-O-benzoyl-6-deoxy-l-altropyranosyl ortho-hexynylbenzoate (7) under the catalysis of PPh3AuNTf2. NMR and molecular modeling studies showed that the pentasaccharide (5) adopted a left-handed helical conformation.
Direct glycosylation of unprotected and unactivated sugars using bismuth nitrate pentahydrate
Polanki, Innaiah K.,Kurma, Siva H.,Bhattacharya, Asish K.
, p. 196 - 205 (2015/06/08)
Bi(NO3)3, a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high α-selectivity. Further, an expedient separation of α- and β-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.