1993
DOI: 10.1016/0008-6215(93)80050-o
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Stereospecific synthesis of 1,2-cis-glycosides of 2-amino sugars

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Cited by 18 publications
(7 citation statements)
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“…Accordingly, coupling of C(2)-hydroxyl group of mannose derivative 18 with C(2)- N -substituted benzylidene donors 5 − 7 provided disaccharides 28 − 30 in good yields (87−97%) and exclusively as the α-isomers (entry 5). With Kochetkov’s C(2)-azido thiocyanate donor, coupling of 18 also afforded the α-isomer as the major product, albeit in lower yield (72%) . When dihydrocholesterol 19 was employed as a nucleophile, the corresponding glycoconjugate 31 was obtained in 85% yield with an 11:1 α:β ratio (entry 6).…”
Section: Resultsmentioning
confidence: 99%
“…Accordingly, coupling of C(2)-hydroxyl group of mannose derivative 18 with C(2)- N -substituted benzylidene donors 5 − 7 provided disaccharides 28 − 30 in good yields (87−97%) and exclusively as the α-isomers (entry 5). With Kochetkov’s C(2)-azido thiocyanate donor, coupling of 18 also afforded the α-isomer as the major product, albeit in lower yield (72%) . When dihydrocholesterol 19 was employed as a nucleophile, the corresponding glycoconjugate 31 was obtained in 85% yield with an 11:1 α:β ratio (entry 6).…”
Section: Resultsmentioning
confidence: 99%
“…This approach, developed by Kochetkov et al, provided complete a-stereoselectivity of glycosylation even in dichloromethane, a reaction solvent that does not typically favor a-glycosylations. 164 For example, coupling of thiocyanate 69, obtained from bromide 68, with 6-O-tritylated glycosyl acceptor 70 in the presence of TrClO 4 provided a-linked disaccharide 71 in 81% yield (Scheme 13).…”
Section: From O-sulfonyl Derivativesmentioning
confidence: 99%
“…Potassium 2-mercaptobenzoxazole 29 (KSBox) (0.600 g, 3.17 mmol) and 18-crown-6 (0.67 g, 0.25 mmol) were added to a stirring solution of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-Dglucopyranosyl bromide 30 (0.50 g, 1.27 mmol) in dry acetone (10 mL), then the reaction mixture was stirred under argon for 2.5 hours at room temperature. Upon completion, the solid was filtered off and rinsed successively with CH 2 Cl 2 .…”
Section: Synthesis Of Glycosyl Donorsmentioning
confidence: 99%