5596-21-4Relevant academic research and scientific papers
Chemo- and regioselective monosulfonylation of nonprotected carbohydrates catalyzed by organotin dichloride under mild conditions
Muramatsu, Wataru
, p. 8083 - 8091,9 (2020/10/15)
The catalytic regioselective monosulfonylation of nonprotected carbohydrates using organotin dichloride under mild conditions is examined. The carbohydrates were chemo- and regioselectively converted to the corresponding monosulfonates in the presence of
Synthesis of Methyl 6-Deoxy-6-diphenylphosphino-α-D-glucopyranoside: Temperature-Dependence of the Primary O-Tosyl Cleavage Mode
Dahlhoff, Wilhelm V.,Radkowski, Karin
, p. 891 - 896 (2007/10/03)
Methyl α-D-glucopyranoside is converted to methyl 6-p-toluenesulfonyl-2,3,4-tris-O-trimethylsilyl-α-D-glucopyranoside 2 and then reacted with lithium diphenylphosphide in THF. When the reaction is carried out at room temperature and below, S-O cleavage dominates giving methyl 2,3,4-tris-O-trimethylsilyl-α-D-glucopyranoside 3, whereas at 60°C in THF or at 35°C in diethyl ether, C-O cleavage occurs yielding the title carbohydrate-phosphine 4 in good yield after deprotection.
Regioselective monotosylation of non-protected and partially protected glycosides by the dibutyltin oxide method
Tsuda,Nishimura,Kobayashi,Sato,Kanemitsu
, p. 2883 - 2887 (2007/10/02)
Tosylation of non-protected glycopyranosides with p-toluenesulfonyl chloride in the presence of 4-dimethylaminopyridine, after activiation of the glycosides by dibutyltin oxide, gave mono-O-tosylates in good yield. The regioselectivity in this tosylation
REGIOSELECTIVE STANNYLATION. ACYLATION OF CARBOHYDRATES: COORDINATION CONTROL
Ogawa, Tomoya,Matsui, Masanao
, p. 2363 - 2370 (2007/10/02)
An efficient method for the regioselective enhancement of the nucleophilicity of polyhydroxy compounds has been developed.Partial stannylation of carbohydrate with (Bu3Sn)2O and subsequent electrophilic attack with benzoyl chloride gave rise to regioselec
