58530-76-0Relevant academic research and scientific papers
Synthesis of 2(R),3-dihydroxypropyl and 2(R),3(R)-dihydroxybutyl β-d-fructopyranosides and some derivatives
Sung'hwa, Fortunatus,Strik, Axel,Regeling, Henk,Zwanenburg, Binne,Chittenden, Gordon J.F.
, p. 846 - 854 (2007/10/03)
The synthesis of 2(R),3-dihydroxypropyl and 2(R),3(R)-dihydroxybutyl β-d-fructopyranosides, and some derivatives, employing Sharpless-type catalytic asymmetric dihydroxylation procedures is described. Some aspects of the reactions, including stereoselecti
Enhanced reactivity of secondary hydroxyl groups in the O-alkylation of carbohydrate-related primary-secondary vic-glycols. Regioselective 2-O-benzylation of 1,3:2,4-di-O-ethylidene-D-glucitol
El'perina, E. A.,Struchkova, M. I.,Serkebaev, M. I.,Serebryakov, E. P.
, p. 744 - 750 (2007/10/02)
Partial O-alkylation of 1,3:2,4-di-O-ethylidene-D-glucitol (1a), 1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose (1b), and R-(+)-1-O-benzylglycerol (1c) with benzyl chloride in a KOH/DMSO system results in products of monoalkylation at the secondary (4a-c) and at the primary hydroxyl (2a-c) in ratios of over 95:5 (a), ca. 2:1 (b), and ca. 1:1 (c), whereas (+/-)propane-1,2-diol (1d) gives only the product of 1-O-benzylation (2d).A qualitatively similar result is observed upon O-alkylation of diols (1a-e) with 2-methoxyethanol tosylate.
Chiral glycerol derivatives
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, (2008/06/13)
Enantiomerically pure glycerol derivatives, e.g. S-1,2-O-isopropylidene, S-1,2-O-benzylidene, and R-1,2-O-dibenzyl glycerol, have been prepared from 1,2R-O-protected erythritols in high yields. The latter compounds are easily obtained from erythorbic acid and are useful building blocks in the synthesis of a host of optically active compounds having biological activity.
ENANTIOSELECTIVE SYNTHESIS OF 2-BENZYLOXY ALCOHOLS AND 1,2-DIOLS VIA ALKYLATION OF CHIRAL GLYCOLATE IMIDES. A CONVENIENT APPROACH TO OPTICALLY ACTIVE GLYCEROL DERIVATIVES
Cardillo, Giuliana,Orena, Mario,Romero, Marta,Sandri, Sergio
, p. 1501 - 1508 (2007/10/02)
The alkylation of the chiral enolates of glycolate imides 2a and 2b proceedes in highly diastereoselective manner to give 2'-substituted products in good yield.Reductive cleavage with LiBH4 affords the corresponding 2-benzyloxyalcohols 3a-c and 11a-b which are successively converted to 1,2-diols in high optical purity.By this method (R)-1-propanoyloxy-2,3-propanediol 9 and (S)-1-tridecyloxy-2,3-propanediol 14, a glyceride extracted from sponges Plocamiidae, have been synthesized, starting from 2a and 2b, respectively.
The Chemistry of L-Ascorbic and D-Isoascorbic Acids. 2. R and S Glyceraldehydes from a Common Intermediate
Mikkilineni, Amarendra B.,Kumar, Praveen,Abushanab, Elie
, p. 6005 - 6009 (2007/10/02)
(R)- and (S)-glyceraldehyde and glycerol derivatives have been prepared from (2R,3S)-1,2-O-isopropylidenebutane-1,2,3,4-tetrol. (2R,3S)- and (2S,3S)-1,2-O-benzylidenebutane-1,2,3,4-tetrol have been prepared and cleaved to give (R)- and (S)-1,2-O-benzylideneglyceraldehydes and -glycerols.The conservation of chirality and conversion to PAF analogues are also demonstrated.
Synthesis and antiherpetic activity of (S)-, (R)- and (±)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine, linear isomers of 2'-nor-2'-deoxyguanosine
Ashton,Canning,Reynolds,Tolman,Karkas,Liou,Davies,DeWitt,Perry,Field
, p. 926 - 933 (2007/10/02)
Racemic 9-[2,3-dihydroxy-1-propoxy)methyl]guanine [(±)-iNDG], a new analogue of acyclovir (ACV) and a structural analogue of 2'-nor-2'-deoxyguanosine (2'NDG), was synthesized and found to inhibit the replication of herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). Subsequently, its optical isomers, (R)- and (S)-iNDG, were prepared from chiral intermediates. The chloromethyl ethers of 1,2-di-O-benzyl-D- and -L-glycerol were made and reacted with tris(trimethylsilyl)guanine to give the 9-alkylated guanines, which were deprotected by catalytic hydrogenolysis. Against HSV-1 and HSV-2 in cell culture, (S)-iNDG was approximately 10- to 25-fold more active than the R enantiomer and had an ED50 comparable to those for ACV and 2'NDG. The inferior activity of (R)-iNDG paralleled the poor inhibition of viral DNA polymerase by its phosphorylation products. In mice infected intraperitoneally or orofacially with HSV-1 or intravaginally with HSV-2, (S)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine [(S)-iNDG] was less efficacious than 2'NDG but comparable to or more active than ACV.
SEPARATION OF RACEMATES OF 1,2-DISUBSTITUTED DERIVATIVES OF GLYCEROL INTO ANTIPODES
Andguladze, M. K.,Kaplun, A. P.,Kulish, M. A.,Shvets, V. I.
, p. 846 - 851 (2007/10/02)
1,2-Di-O-Benzyl-rac-glycerol (or 1-stearoyl-2-O-benzyl-rac-glycerol) was glycocylated with acetobromoglucose or mannose tert-butyl orthoacetate.The chromatographic chasracteristics of the synthesized 1,2-trans-glycosides and of the glycosides obtained by
INVESTIGATION IN THE FIELD OF GLYCOSYL DIGLYCERIDES. IX.* SYNTHESIS OF FLUORESCENE-LABELED GLYCOSYL DIGLYCERIDES
Anguladze, M. K.,Kaplun, A. P.,Shvets, V. I.
, p. 2075 - 2080 (2007/10/02)
Glucosyl diglyceride having the natural structure with a fluorescent label in the hydrophobic part of the molecule was synthesized from 1-stearoyl-2-O-benzyl-rac-glycerol.The glucosyl diglyceride labeled in the hydrophilic part was obtained by dansylation
