146608-95-9Relevant academic research and scientific papers
A 2,4-O-[(Z)-2-butenylene]-bridged glucopyranose: efficient construction of the bicyclic skeleton and its axial-rich twist-boat conformation
Cao, Yang,Kasai, Yusuke,Bando, Masafumi,Kawagoe, Mayumi,Yamada, Hidetoshi
experimental part, p. 2574 - 2578 (2009/09/05)
Synthesis and conformational analyses of 1-O-acetyl-3,6-di-O-benzyl-2,4-O-[(Z)-2-butenylene]-β-d-glucopyranose are described. The construction of the trioxabicyclo[6.3.1]dodecane skeleton of the compound was initiated from a ring-opened glucose, followed
Convenient construction of a variety of glycosidic linkages using a universal glucosyl donor
Sato, Ken-Ichi,Akai, Shoji,Sakai, Koudai,Kojima, Masaru,Murakami, Hideshige,Idoji, Tetsuya
, p. 7411 - 7414 (2007/10/03)
This letter deals with the concept of constructing four types (cis-α, trans-α, cis-β, and trans-β) of glycosidic linkages using a universal glucosyl donor. The selectively protected universal glucosyl donor 8 was synthesized in 36% yield from d-glucose (eight steps). The donor 8 undergoes glycosidation with a primary carbohydrate alcohol 7 to give disaccharide 9 having a 1,2-cis-α-glycosidic linkage in 90% yield. The construction of the corresponding 1,2-trans-α-glycosidic linkage was performed in 68% yield (three steps) from 9. A similar glycosidation of the 2-O-(N- phenylcarbamoyl)-glucosyl donor 6 derived from 8 with 7 gave disaccharide 11 having a 1,2-trans-β-glycosidic linkage in 75% yield. The construction of the corresponding 1,2-cis-β-linkage was performed in 53% yield (three steps) from 11.
Synthesis of a di- and a trisaccharide related to the antigen from Klebsiella type 43
Sarbajna, Sumita,Misra, Anup K.,Roy, Nirmolendu
, p. 2559 - 2570 (2007/10/03)
Starting from D-galactose, D-mannose and D-glucose methyl α-D- galactopyranosyl-(1→3)-α-D-mannopyranosyl-(1→2)-α-D-mannopyranoside and allyl β-D-mannopyranosyl-(1→4)-β-D-glucopyranosyl uronate were synthesised in a highly stereoselective manner.
Synthesis of the tetrasaccharide repeating unit of the antigen from Escherichia coli O126 as its methyl glycoside
Misra, Anup Kumar,Roy, Nirmolendu
, p. 1047 - 1056 (2007/10/03)
The tetrasaccharide repeating unit (17) of the antigen from E. coli O126 has been synthesized as its methyl glycoside by sequential addition of monosaccharide derivatives. The formation of the β-mannosidic linkage was achieved by Swern oxidation of the gl
Synthesis of a pentasaccharide corresponding to the repeating unit of the exopolysaccharide from Cryptococcus neoformans serovar D
Zegelaar-Jaarsveld, Korien,Smits, Sander A. W.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 1819 - 1832 (2007/10/03)
The assembly of the pentasaccharide repeating unit of the exopolysaccharide from Cryptococcus neoformans serovar D (i.e. 1) is described. The glucuronic acid residue in 1 is introduced as a glucopyranoside and oxidized in a later stage of the synthesis. Thus, iodonium ion-assisted glycosylation of the partially protected methyl mannopyranoside 11 with ethylthio donor 14 gave, after selective deprotection, disaccharide 18. Elongation of the latter with D-glucopyranoside 35 gave trisaccharide 36. Subsequent protective group manipulations yielded the acceptor 37. Condensation of disaccharide donor 31 with trisaccharide acceptor 37 yielded pentasaccharide 38. Protective group manipulations of 38 afforded 42, the glucoside of which was oxidized to yield the corresponding glucuronide 44. Hydrogenolysis of 44 gave the target pentasaccharide 1.
Synthetic Studies toward Pyruvate Acetal Containing Saccharides. Synthesis of the Carbohydrate Part of the Mycobacterium smegmatis Pentasaccharide Glycolipid and Fragments Thereof for the Preparation of Neoantigens
Ziegler, Thomas,Eckhardt, Elisabeth,Birault, Veronique
, p. 1090 - 1099 (2007/10/02)
A series of 2,3-di-O-benzoyl-4,6-O--D-glucopyranosyl donors (β-phenylthio 3, bromide 4, α-chloride 5, β-fluoride 6, and trichloroacetimidate 7) were prepared from the corresponding α-allyl glucoside 1 via the deallylated glucose 2 and were tested in glycosylation reactions with methanol to give the pyruvylated methyl glucosides 8 and 9 and with methyl 2,4,6-tri-O-benzoyl-β-D-glucopyranoside 10 to give the disaccharide 11.Best result with respect to yield and β-selectivity of the coupling were achieved with imidate 7.Thus, the 2-O-benzoyl-4,6-O--3-O-methyl-D-glucopyranosyl trichloroacetimidate 14 was prepared from its benzyl glucoside 12 and used for the synthesis of fragments related to the Mycobacterium smegmatis lipopentasaccharide.Trimethylsilyl trifluoromethanesulfonate-mediated condensation of 14, 5-pentanol, and 10, respectively, followed by deblocking of the products 15 and 17 gave the pyruvylated aminopentyl glucoside 16 and methyl laminaribioside 18.Treatment of 17 with dichloromethyl methyl ether gave the laminaribiosyl chloride 19, coupling of which with protected 5-aminopentanol gave 20 also obtained from 14 and the monosaccharide nucleophile 26.The trisaccharide 5-aminopentyl glycoside fragment 42 was prepared by first coupling of 14 and benzyl 2-O-benzoyl-4,6-O--α-D-glucopyranoside 30 that was converted to the bispyruvylated laminaribiose imidate 33, followed by condensation with thioglycoside 38 obtainable in four steps from 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose to give the trisaccharide ethyl thioglycoside 40.Next, NIS-mediated condensation of 40 and 5-pentanol followed by deblocking gave 42.Pentasaccharide 45 was similarly prepared from 40 and hepta-O-benzoyltrehalose 43 to give first the blocked saccharide 44, deblocking of which afforded the target pentasaccharide.
