65372-02-3Relevant academic research and scientific papers
Glycosylation with 2-Acetamido-2-deoxyglycosyl Donors at a Low Temperature: Scope of the Non-Oxazoline Method
Arihara, Ryoichi,Kakita, Kosuke,Suzuki, Noritoshi,Nakamura, Seiichi,Hashimoto, Shunichi
, p. 4259 - 4277 (2015/05/13)
A direct construction of 1,2-trans-β-linked 2-acetamido-2-deoxyglycosides was investigated. The 3,4,6-tri-O-benzyl- and 3,4,6-tri-O-acetyl-protected glycosyl diethyl phosphites and 4,6-O-benzylidene-protected galactosyl diethyl phosphite each reacted with
Formation of 2-acetamido-2-deoxy-d-glucopyranosidic linkages via glycosidation using a combination of two lewis acids
Oda, Yoshiki,Midorikawa, Masanobu,Yamanoi, Takashi
, p. 198 - 215 (2015/03/04)
A mixed activation system composed of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promotes the glycosylation of various alcohol acceptors using 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl ac
A practical synthesis of various 2-deoxy-N-glycosides by using D-glucal
Meyerhoefer, Terence J.,Kershaw, Sonia,Caliendo, Nadia,Eltayeb, Sumeia,Hanawa-Romero, Emi,Bykovskaya, Polina,Huang, Victor,Marzabadi, Cecilia H.,De Castro, Michael
supporting information, p. 2457 - 2462 (2015/04/22)
We herein report the synthesis of 2-deoxy-2-iodo-glycosylamides, glycosylurea, N-glycosylbenzotriazole, and N-glycosyl imidazole by addition reaction of trimethylsilyl amides, imidazoles, and benzotriazoles to D-glucal in the presence of N-iodosuccinimide and propionitrile at 0 C. Two diastereomers were isolated - the α-mannose and β-gluco isomers. Reduction and substitution reaction of the iodine at position C-2 led to formation of various 2-deoxy-N-glycosides and 2-hydroxy-β-D-glucopyranosylamide. The newly generated compounds were screened for their inhibitory activity against various enzymes that included Nav1.7 sodium ion voltage-gated channel in HEK293 cells and the results are discussed.
Direct and stereoselective synthesis of 2-acetamido-2-deoxy-β-D- glycopyranosides by using the phosphite method
Arihara, Ryoichi,Nakamura, Seiichi,Hashimoto, Shunichi
, p. 2245 - 2249 (2007/10/03)
(Chemical Equation Presented) Avoiding the intermediate: The β-selective glycosidation of 2-acetamido-2-deoxyglycosyl diethyl phosphites promoted by bis(trifluoromethanesulfonyl)imide (Tf2NH) proceeds in a direct manner and does not afford an o
C2-Acetamidomannosylation. Synthesis of 2-N-acetylamino-2-deoxy-α-D-mannopyranosides with glucal donors
Liu, Jing,Di Bussolo, Valeria,Gin, David Y.
, p. 4015 - 4018 (2007/10/03)
A one-pot C2-acetamidomannosylation reaction for the synthesis of 2-N-acetylamino-2-deoxy-α-D-mannopyranosides from glucals is described. Glucal donors are activated by the reagent combination of 2,8-dimethyldibenzothiophene-5-oxide (DMDBTO) and trifluoromethanesulfonic anhydride. Upon subsequent addition of N-(TMS)acetamide and an appropriate glycosyl acceptor, the corresponding C2-acetamidomannopyranosides are formed.
C2-amidoglycosylation. Scope and mechanism of nitrogen transfer
Liu, Jing,Gin, David Y.
, p. 9789 - 9797 (2007/10/03)
A one-pot C2-amidoglycosylation reaction for the synthesis of 2-N-acyl-2-deoxy-β-pyranosides from glycals is described. Glycal donors activated by the reagent combination of thianthrene-5-oxide (11) and Tf2O, followed by treatment with an amide nucleophile and a glycosyl acceptor, lead to the formation of various C2-amidoglycoconjugates. Both the C2-nitrogen transfer and the glycosidic bond formation proceed stereoselectively, allowing for the introduction of both natural and nonnatural amide functionalities at C2 with concomitant anomeric bond formation in a one-pot procedure. Tracking of the reaction by low-temperature NMR spectroscopy employing 15N- and 18O-isotope labels suggests a mechanism involving the formation of the C2-sulfonium glycosyl imidate 39 as well as oxazoline 37 as key intermediates in this novel oxidative glycosylation process.
Glycosylidene carbenes. Part 22. α-D-Selectivity in the glycosidation by carbenes derived from 2-acetamido-hexoses
Vasella,Witzig
, p. 1971 - 1982 (2007/10/02)
Glycosylidene carbenes derived from the GlcNAc and AllNAc diazirines 1 and 3 were generated by thermolysis or photolysis of the diazirines. The reaction of 1 with i-PrOH gave exclusively the isopropyl α-D-glycoside of 5 besides some dihydrooxazole 9. A similar reaction with (CF3)2CHOH yielded predominantly the α-D-anomer of 6, while glycosidation of 4-nitrophenol (→7) proceeded with markedly lower diastereoselectivity. Similarly, the allo-diazirine 3 gave the corresponding glycosides 12-14, but with a lower preference for the α-D-anomers. The reactions of the carbene derived from 1 with Ph3COH (→8) and diisopropylideneglucose 10 (→11) gave selectively the α-D-anomers. The α-D-selectivity increases with increasing basicity (decreasing acidity) of the alcohols. It is rationalized by an intermolecular H-bond between the acetamido group and the glycosyl acceptor. This H-bond increases the probability for the formation of a 1,2-cis-glycosidic C-O bond. The gluco-intermediates are more prone to forming a N-H···(H)OR bond than the allo-isomers, since the acetamido group in the N-acetylallosamine derivatives forms an intramolecular H-bond to the cis-oriented benzyloxy group at C(3), as evidenced by δ/T and δ/c experiments.
O-BENZYLATED OXAZOLINE DERIVATIVES OF 2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE FROM 1-PROPENYL GLYCOSIDES. SYNTHESIS OF THE PROPENYL GLYCOSIDES AND THEIR DIRECT CYCLIZATION
Nashed, Mina A.,Slife, Charles W.,Kiso, Makoto,Anderson, Laurens
, p. 237 - 252 (2007/10/02)
1-Propenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α- and -β-D-glucopyranosides (3α, 3β) were obtained by the successive isomerization and acetylation of the known allyl glycosides 1α and 1β.The allyl glycosides were also converted, via their benzylidene 4
