197716-38-4Relevant academic research and scientific papers
Iodine monochloride (ICl) as a highly efficient, green oxidant for the oxidation of alcohols to corresponding carbonyl compounds
Wei, Peng,Zhang, Datong,Gao, Zhigang,Cai, Wenqing,Xu, Weiren,Tang, Lida,Zhao, Guilong
supporting information, p. 1457 - 1470 (2015/05/20)
Iodine monochloride (ICl) was discovered to be a highly efficient, green oxidant, which can oxidize aldose hemiacetals, diarylmethanols, arylalkylmethanols, anddialkylmethanols to the corresponding aldose lactones, diarylmethanones, arylalkylmethanones, and dialkylmethanones, respectively, in high yields. ICl as a green, metal-free oxidant is characterized by mild reaction condition, short reaction time, good yield, and broad scope.
An expeditious synthesis of an analogue of (-)-steviamine by way of the 1,3-dipolar cycloaddition of a nitrile oxide with a 1-C-allyl iminosugar
Chronowska, Aleksandra,Gallienne, Estelle,Nicolas, Cyril,Kato, Atsushi,Adachi, Isao,Martin, Olivier R.
scheme or table, p. 6399 - 6402 (2011/12/22)
In our continuing effort to develop inhibitors of the mycobacterial galactan biosynthesis, we planned to synthesize original iminosugar-based analogues of UDP-galactofuranose by way of the 1,3-dipolar cycloaddition reaction between a 1-C-allyl iminosugar and a nitrile oxide, followed by the reductive cleavage of the resulting isooxazoline. In initial studies, it was found that this last step led in one pot to a new poly-hydroxylated indolizidine derivative closely related to the recently isolated (-)-steviamine, in good yield, by way of a sequence involving at least five individual reactions. The activity of this new compound as a glycosidase inhibitor was evaluated against a panel of glycosidases and compared to (-)-steviamine.
An olefin metathesis route for the preparation of (1 → 6)-linked C-disaccharide glycals. A convergent and flexible approach to C-saccharide synthesis
Postema, Maarten H. D.,Calimente, Daniel,Liu, Lei,Behrmann, Tonja L.
, p. 6061 - 6068 (2007/10/03)
A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (1a-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.
Thiosugars, 2: Preparation of 2,3,5-tri-O-benzyl-4-thio-L-arabino- furanosides and the corresponding 4'-thionucleoside analogues
Wirsching, Joern,Voss, Juergen
, p. 691 - 696 (2007/10/03)
1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-arabino-furanose (9) has been prepared from D-xylose via the 1,4-dithio-L-arabino-furanoside 8. The crucial step of the reaction, i.e. the intramolecular cyclization of the open-chain dithioacetal 5, has been achieved in a yield of 90% by applying tetrabutylammonium iodide as promoter. Reaction of 9 with bis(trimethylsilyl)uracil or -thymine led to the benzyl derivatives 12 and 13 from which the deprotected 4'-thionucleoside analogues 14 and 15 have been prepared by debenzylation with boron tribromide.
Synthesis of L-enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides
Satoh, Hiroshi,Yoshimura, Yuichi,Sakata, Shinji,Miura, Shinji,Machida, Haruhiko,Matsuda, Akira
, p. 989 - 992 (2007/10/03)
L-Enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides were synthesized from D-xylose. Methyl 2,3,5-tri-O-benzyl-D-xylofuranoside 6 was converted to the corresponding xylitol 7, which was treated with MsCl and then Na2S to give 1,4-anhydro-L-4-thioarabitol 8. As previously reported, Pummerer rearrangement of 8 followed by glycosylation with a silylated thymine and N4-acetylcytosine derivative and deprotection gave the corresponding α- and β-L-4'-thioarabinofuranosyl pyrimidine nucleosides.
Novel asymmetric synthesis of an indolizidine alkaloid, (+)-lentiginosine employing highly stereoselective hydrogenation of α-hydroxypyrrolidine
Yoda, Hidemi,Kawauchi, Miho,Takabe, Kunihiko
, p. 137 - 138 (2007/10/03)
An efficient and novel process is described for the asymmetric synthesis of a (1S,2S,8aS)-dihydroxyindolizidine alkaloid, (+)-lentiginosine in which the asymmetric deoxygenation of the quaternary α-hydroxypyrrolidine derivative derived from D-xylose is used as a key step.
Formal synthesis of (-)-syringolide 1 starting from D-xylose based on a biomimetic strategy
Yoda, Hidemi,Kawauchi, Miho,Takabe, Kunihiko,Hosoya, Ken
, p. 1895 - 1898 (2007/10/03)
An expeditious and practical synthertic process for a nonproteinaceous elicitor, (-)-syringolide 1, has been developed in a short number of steps utilizing the putative biosynthetic pathway by featuring the elaboration of the protected D-xylose as a starting material.
Immunostimulatory and antitumor activities of monoglycosylceramides having various sugar moieties
Motoki,Morita,Kobayashi,Uchida,Akimoto,Fukushima,Koezuka
, p. 1487 - 1491 (2007/10/03)
Ten kinds of monoglycosylceramides (MonoCers), having the same ceramide portion and different sugar moieties, were synthesized and their immunostimulatory and antitumor activities were examined. The manner of combination between sugar and ceramide has been demonstrated to affect the manifestation of immunostimulatory and resultant antitumor activities of MonoCers, and in the case of D-MonoCers having the D-sugar, α-D-MonoCers (sugar combined to ceramide in an α-configuration) show stronger activities than β-D-MonoCers. Furthermore, the form of sugar, not the furanose-form but the pyranose-form, and the 2- and 4-hydroxyl groups of the pyranose-form of sugar, seemed to play an important role in the manifestation of the activities of α-D-MonoCers.
C-glycofuranosides via tandem Wittig-Michael sequence using a thiazole-armed phosphorane. A route to C-furanosyl α-hydroxy propanals and propionic acids
Dondoni, Alessandro,Marra, Alberto
, p. 7327 - 7330 (2007/10/02)
The reactions of 2-thiazolylcarbonylmethylenetriphenylphosphorane with five protected D-furanoses (manno, ribo, arabino, xylo, and lyxo) in refluxing toluene lead to mixtures of α- and β-1-C-(2-thiazolacyl)-glycosides (66-93 % overall yield). The β-linked C-glycosides derived from 2,3:5,6-di-O-isopropylidene-D-mannnofuranose was reduced to (R) and (S) akohols which after protection as O-benzyl ethers were transformed to α-alkoxy aldehydes by thiazole-to-formyl conversion; the aldehydes were oxidized to the corresponding α-alkoxy acids.
POTENT COMPETITIVE INHIBITION OF &α-GALACTOSIDASE AND &α-GLUCOSIDASE ACTIVITY BY 1,4-DIDEOXY-1,4-IMINOPENTITOLS: SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL AND OF BOTH ENANTIOMERS OF 1,4-DIDEOXY-1,4-IMINOARABINITOL
Fleet, G. W. J.,Nicholas, S. J.,Smith, P. W.,Evans, S. V.,Fellows, L. E.,Nash, R. J.
, p. 3127 - 3130 (2007/10/02)
The syntheses of 1,4-dideoxy-1,4-imino-D-lyxitol (3), 1,4-dideoxy-1,4-imino-D-arabinitol (4) and 1,4-dideoxy-1,4-imino-L-arabinitol (5) are reported; (3) is a potent competitive inhibitor of α-galactosidase (green coffee beans) and (4) a competitive inhibitor of α-glucosidase (Brewer's yeast) suggesting that iminopentitols have considerable potential as glycosidase inhibitors. (4) was found to be identical to an alkaloid recently isolated from Angylocalyx boutiqueanus.
