52079-85-3Relevant academic research and scientific papers
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 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.
Strain-Directed Bridge Cleavage of (Phenylsulfonyl)-7-oxabicycloheptane Derivatives: Application to the Total Synthesis of Carba-α-DL-glucopyranose
Acena, Jose Luis,Arjona, Odon,Pradilla, Roberto Fernandez de la,Plumet, Joaquin,Viso, Alma
, p. 1945 - 1946 (2007/10/02)
New methodology to prepare highly oxygenated cyclohexenylsulfones by regioselective β-elimination of (phenylsulfonyl)-7-oxabicycloheptane derivatives has been developed, and its application to the total synthesis of carba-α-DL-glucopyranose is desc
SYNTHESIS OF FOUR NEW DIASTEREOISOMERS OF DL-5-HYDROXYMETHYL-1,2,3,4-CYCLOHEXANETETROL
Ogawa, Seiichiro,Tsukiboshi, Yoshiki,Iwasawa, Yoshikazu,Suami, Tetsuo
, p. 77 - 90 (2007/10/02)
Four new diastereoisomers of the pseudo-sugar DL-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol, having (1,2,3,4/5)- (2), (1,5/2,3,4)- (3), (1,2,3/4,5)- (4), and (1,2,4,5/3)-configurations (5), have been synthesised by unambiguous sequences from readily availa
TOTAL SYNTHESIS OF (+)-(1,2,3/4,5)-2,3,4,5-TETRAHYDROXYCYCLOHEXANE-1-METHANOL AND (+)-(1,3/2,4,5)-5-AMINO-2,3,4-TRIHYDROXYCYCLOHEXANE-1-METHANOL . X-RAY CRYSTAL STRUCTURE OF (3s)-(+)-2-EXO-BROMO-4,8-DIOXATRICYCLO3,7>NONA
Ogawa, Seiichiro,Iwasawa, Yoshikazu,Suami, Tetsuo,Ohba, Shigeru,Ito, Masatoki,Saito, Yoshihiko
, p. 903 - 906 (2007/10/02)
The optical resolution of (+/-)-7-endo-oxabicyclohept-5-ene-2-carboxylic acid (+/-)-1 has been accomplished by use of (R)-(+)- and (S)-(-)-α-methylbenzylamine, respectively.The absolute configuration of (-)-(1) has been determined on the basis of X
Cyclitol Reactions, X. - Synthesis of Enantiomerically Pure Pseudo-α-D-galactopyranose and Pseudo-β-D-mannopyranose
Paulsen, Hans,Deyn, Wolfgang von,Roeben, Wolfgang
, p. 433 - 449 (2007/10/02)
The L-chiro-inositol 2, prepared from quebrachitol, is transferred, via 5, into the inosose 7.Wittig reaction of 7 and subsequent hydroboration followed by oxidation leads to the hydroxymethyl branched-chain derivative 8.From this, via 11, the S-methyl di
TOTAL SYNTHESIS AND ABSOLUTE CONFIGURATION OF (+)-(1,2,3/4,5)-2,3,4,5-TETRAHYDROXY-1-CYCLOHEXANEMETHANOL
Ogawa, Seiichiro,Iwasawa, Yoshikazu,Suami, Tetsuo
, p. 355 - 356 (2007/10/02)
The title branched-chain cyclitol has been synthesized from chiral 7 endo-oxabicyclohept-5-ene-2-carboxylic acid, the absolute configuration of which was established on the basis of X-ray analysis of crystalline bromolactone derived from it.From th
