52079-86-4Relevant academic research and scientific papers
A stereodivergent approach to 5a-carba-α-D-gluco-, -α-D-galacto and -β-L-gulopyranose pentaacetates from D-mannose, based on 6-exo-dig radical cyclization and Barton-Mccombie radical deoxygenation
Gomez, Ana M.,Moreno, Eduardo,Valverde, Serafin,Lopez, J. Cristobal
, p. 1830 - 1840 (2007/10/03)
The three carbasugars, 5a-carba-α-D-gluco-, -α-D-galacto and -β-L-gulopyranose pentaacetates 42, 35 and 28 respectively, have been prepared in a stereodivergent manner from D-mannose. Alkynyl derivatives of 2,3:4,6-di-O-isopropylidene-D-mannopyranose, whi
A general stereodivergent strategy for the preparation of carbasugars. Syntheses of 5a-carba-α-D-glucose, α-D-galactose, and β-L-gulose pentaacetates from D-mannose
Ning, Jun,Yi, Yuetao,Kong, Fanzuo
, p. 5559 - 5562 (2007/10/03)
A stereodivergent approach to 5a-carba-D- and L-pyranoses has been applied to the preparation of 5a-carba-α-D-gluco-, 5a-carba-α-D-galacto-, and 5a-carba-β-L-gulopyranose pentaacetates. The strategy, by which a single precursor can be transformed into thr
Synthesis of an ether-linked alkyl 5a-carba-β-D-glucoside, a 5a-carba-β-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-D-glucoside, and an alkyl 5a′-carba-β-lactoside
Ogawa, Seiichiro,Aoyama, Hiroshi,Sato, Toshinori
, p. 1979 - 1992 (2007/10/03)
For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-β-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine), in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-β-D-galactose residue into the 4-position of dodecyl β-D-glucopyranoside. A strong and specific inhibition of β-galactosidase (Ki 0.67 μM, bovine liver) was found for dodecyl 5a-carba-β-D-galactopyranoside.
A general norbornyl based synthetic approach to carbasugars and 'confused' carbasugars
Mehta, Goverdhan,Talukdar, Pinaki,Mohal, Narinder
, p. 7663 - 7666 (2007/10/03)
The norbornyl system has been recognized simply as a 'locked' carbasugar and a short, general approach to carbasugars and their new siblings, 'confused' carbasugars, from readily available 7-ketonorbornanes is reported.
A norbornyl route to cyclohexitols: Structural diversity in fragmentation through functional group switching. Synthesis of α- and β- galactose, α-talose and α-fucopyranose carbasugars
Mehta, Goverdhan,Mohal, Narinder,Lakshminath, Sripada
, p. 3505 - 3508 (2007/10/03)
A novel fragmentation sequence has been executed within the norbornane system, involving C1-C7 bond scission, to extract a versatile, highly functionalized cyclohexanoid moiety. Its further evolution towards a range-of carbasugars is described. (C) 2000 Elsevier Science Ltd.
Desymmetrisation of dienylsilanes. Stereoselective access to cyclitols and carba-sugars
Landais, Yannick
, p. 104 - 111 (2007/10/03)
The diastereo- and enantioselective functionalisation of 1,4-cyclohexadienylsilanes using Sharpless asymmetric dihydroxylation and aminohydroxylation offers a straightforward access to various classes of potent inhibitors of glycosidases. The scope and limitation of this desymmetrisation method is illustrated here with the synthesis of various conduritols, carba-sugars and carba-C-disaccharides.
Synthesis of pseudo-sugars based on desymmetrization of dienylsilanes
Angelaud, Remy,Landais, Yannick
, p. 8841 - 8844 (2007/10/03)
A synthesis of pseudo-sugars using the desymmetrization of a dienylsilane, followed by a stereocontrolled introduction of the hydroxymethyl group at C5, is described. The CH2OH group at C5 was elaborated using either a regioselective cyclopropane-ring opening or a [2,3]-Wittig rearrangement.
SYNTHESIS OF SOME DERIVATIVES OF PSEUDO-α-GALACTOPYRANOSE
Ogawa, Seiichiro,Shibata, Yasushi,Miyazawa, Keiko,Toyokumi, Tatsushi,Iida, Tatsuo,Suami, Tetsuo
, p. 53 - 62 (2007/10/02)
Isopropylidenation of DL-(1,2/3,4,5)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol (1) with 2,2-dimethoxypropane in N,N-dimethylformamide in the presence of toluene-p-sulfonic acid gave the 1,2:3,4-, 1,2:4,7-, and 2,3:4,7-di-O-isopropylidene derivatives.Several C-7 substituted derivatives of 1 of biological interest have been prepared by nucleophilic displacement reactions of the tosylate derived from the most readily avaible 1,2:3,4-di-O-isopropylidene derivative 3.Condensation of 3 with 2,3,4,6-tera-O-acetyl-α-D-glucopyranosyl bromide gave diastereoisomeric products, which were converted into 7-O-(β-D-glucopyranosyl)-pseudo-α-D- (26A) and -L-galactopyranose (26B), the structures of which were confirmed by degradation of the octa-acetate of 26A, yielding the know pseudo-α-D-galactopyranose penta-acetate.
