105139-04-6Relevant articles and documents
A Stereoselective Synthesis of an Imino Glycal: Application in the Synthesis of (–)-1-epi-Adenophorine and a Homoimindosugar
Chennaiah, Ande,Dahiya, Amit,Dubbu, Sateesh,Vankar, Yashwant D.
, p. 6574 - 6581 (2018)
A concise stereoselective synthesis of an imino glycal is described in 8 steps starting from 1,2-anhydro-3,4,6-tri-O-benzyl-d-glucopyranose. The utility of the imino glycal has been demonstrated in synthesis of (–)-1-epi-adenophorine and a homoiminosugar
Synthesis of D-glycopyranosyl azides from 1,2-anhydrosugars using lithium azidohydridodiisobutylaluminate
Lee, Goo Soo,Min, Hye Kyung,Chung, Bong Young
, p. 543 - 544 (1999)
1,2-Anhydrosugars were transformed regio- and stereoselectively into the corresponding D-glycopyranosyl azides in high yield by treatment with lithium azidohydridodiisobutylaluminate in THF.
Epoxidation of glycals with oxone-acetone-tetrabutylammonium hydrogen sulfate: A convenient access to simple β-D-glycosides and to α-D-mannosamine and D-talosamine donors
Lafont, Dominique,D'Attoma, Joseph,Gomez, Rejane,Goekjian, Peter G.
, p. 1197 - 1204 (2011/10/19)
The addition of a phase transfer catalyst during the epoxidation of perbenzylated glycals with oxone- acetone under biphasic conditions allows their complete epoxidation. The epoxides were readily transformed into methyl 1,2-trans-β-D-glycosides or 1,2-trans-β-D-glycopyranosyl azides (D-gluco and-D-galacto configurations) bearing a free hydroxyl group at the 2-position. These glycosyl azides were converted to alkyl 1,2-trans-2-acetamido- 2-deoxy-α-D-pyranosides or alkyl 2-allyloxycarbonylamino-2- deoxy-α-D-pyranosides (D-manno and D-talo configurations) by a Staudinger reaction and a double inversion of configuration at C-1 and C-2.
Ceric ammonium nitrate-catalyzed azidation of 1,2-anhydro sugars: Application in the synthesis of structurally diverse sugar-derived morpholine 1,2,3-triazoles and 1,4-oxazin-2-ones
Reddy, Y. Suman,John Pal,Gupta, Preeti,Ansari, Alafia A.,Vankar, Yashwant D.
experimental part, p. 5972 - 5984 (2011/10/08)
Azidation of 1,2-anhydro sugars with NaN3 in CH3CN by using a catalytic amount of ceric ammonium nitrate has been accomplished in a regio- and stereoselective manner. Various 1,2-anhydro sugars produced 2-hydroxy-1-azido sugars in good yields which, in turn, were converted to structurally diverse sugar-derived morpholine triazoles and sugar oxazin-2-ones. These sugar derivatives were tested against various commercially available glycosidases, and two of them were found to be active in the micromolar range.
C2-hydroxyglycosylation with glycal donors. Probing the mechanism of sulfonium-mediated oxygen transfer to glycal enol ethers
Honda, Eiji,Gin, David Y.
, p. 7343 - 7352 (2007/10/03)
The C2-hydroxyglycosylation reaction employing the reagent combination of a diaryl sulfoxide and triflic anhydride offers a novel method for glycal assembly whereby a hydroxyl functionality is stereoselectively installed at the C2-position of a glycal donor with concomitant glycosylation of a nucleophilic acceptor. Mechanistic investigations into this reaction revealed a novel process for sulfonium-mediated oxidation of glycal enol ethers in which the sulfoxide oxygen atom is stereoselectively transferred to the C2-position of the glycal. 18O-labeling studies revealed that the S-to-C2 oxygen-transfer process involves initial formation of a C1-O linkage followed by O-migration to C2, leading to the generation of an intermediate glycosyl 1,2-anhydropyranoside that serves as an in situ glycosylating agent. These findings are consistent with the initial formation of a C2-sulfonium-C1-oxosulfonium pyranosyl species upon activation of the glycal donor with Aryl2SO·Tf2O.
