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.
A Novel Transformation of Four Aldoses to Some Optically Pure Pseudohexopyranoses and a Pseudopentofuranose, Carboxylic Analogues of Hexopyranoses and Pentofuranose. Synthesis of Derivatives of (1S,2S,3R,4S,5S)-, (1S,2S,3R,4R,5S)-, (1R,2R,3R,4R,5S)-, (1S,
Tadano, Kin-ichi,Maeda, Hiroo,Hoshino, Masahide,Iimura, Youichi,Suami, Tetsuo
, p. 1946 - 1956 (2007/10/02)
Knoevenagel reactions with dimethyl malonate of the suitably protected acylic aldehydes 6, 20, 34, and 46, which were prepared from D-ribose, D-xylose, D-arabinose, and D-erythrose, respectively, proceeded smoothly to provide α,β-unsaturated diesters 7, 2
