400091-17-0Relevant articles and documents
Regioselective mono and multiple alkylation of diols and polyols catalyzed by organotin and its applications on the synthesis of value-added carbohydrate intermediates
Xu, Hengfu,Ren, Bo,Zhao, Wei,Xin, Xiaoting,Lu, Yuchao,Pei, Yuxin,Dong, Hai,Pei, Zhichao
, p. 3490 - 3499 (2016/06/06)
A catalytic amount of dibutyltin dichloride was used to develop regioselective alkylation of diols and multiple alkylation of polyols. Alkyl groups, including allyl, alkynyl and long-chain alkyl groups, were successfully introduced to one or two hydroxyl
Directed and efficient syntheses of β(1→4)-linked galacto-oligosaccharides
Lichtenthaler, Frieder W.,Oberthuer, Markus,Peters, Siegfried
, p. 3849 - 3869 (2007/10/03)
Straightforward, preparatively efficient procedures are described for the construction of β(1→4)-intergalactosidic linkages up to the hexasaccharide level. Key elements were the use of phenylthio and/or phenyl sulfoxide functionalities for glycosylations and a judiciously designed blocking group pattern for donor and acceptor alike: pivaloyl protection at O-2 for securing β-selectivity, sterically undemanding allyl or benzyl groups at O-3 and O-6 to minimise the steric bulk around the unreactive galactosyl-4-OH, the p-methoxyphenyl moiety, readily replaceable by SPh, as an intermediate anomeric substituent, and an acetyl group for temporary protection of the terminal Gal-4-OH. This strategy lends itself to iterative block synthesis and interchange of donors and acceptors, thereby demonstrating the broad scope and generality of the overall approach. Although predicted by molecular modelling, inclinations towards starch-like coiling could not so far be verified in any of the galacto-tetra-, -penta-, or -hexaoses or their p-methoxyphenyl glycosides.