130861-06-2Relevant academic research and scientific papers
Zinc-mediated fragmentation of methyl 6-deoxy-6-iodo-hexopyranosides
Skaanderup, Philip R.,Hyldtoft, Lene,Madsen, Robert
, p. 467 - 472 (2002)
An improved procedure was developed for the zinc-mediated fragmentation of protected and unprotected methyl 6-deoxy-6-iodo-hexopyranosides. The method employs sonication of the iodoglycoside with zinc dust in a THF/H2O mixture.
Tri-n-butyltin cuprate as a tool for the preparation of stannyl derivatives of carbohydrates
Jarosz, Slawomir
, p. 10765 - 10774 (1997)
Reaction of tri-n-butyltin cuprate with sterically hindered allylbromides 10(E) and 10(Z) derived from D-galactose led exclusively to S(N)2 products - allyl tributylstannyl sugars 11(E) and 11(Z) in good yield and with retention of the configuration of th
Vitamin b12 catalysis of zinc-mediated 6-deoxy-6-iodopyranoside fragmentation: A mild and convenient preparation of ω-unsaturated hexose derivatives (5-hexenoses)
Kleban, Martin,Kautz, Ulrich,Greul, J?rg,Hilgers, Petra,Kugler, Rolf,Dong, Han-Qing,J?ger, Volker
, p. 1027 - 1033 (2000)
The known zinc-mediated preparation of 5-hexenoses by fragmentation of 6-iodopyranosides can be performed in a simple, fast, and mild way, with less side reactions, when vitamin B12 is employed as a catalyst.
Application of tri-n-butyltin cuprate in sugar chemistry
Jarosz, Slawomir
, p. 3063 - 3066 (1996)
Reaction of sugar allyl bromides with tri-n-butylin cuprate gives sugar allyltin derivatives with retention of the configuration of the double bond, that enables to prepare pure trans or cis olefins. Sugar aldehydes of the general formula Sug-CHO react al
Structure–Activity Studies of N-Butyl-1-deoxynojirimycin (NB-DNJ) Analogues: Discovery of Potent and Selective Aminocyclopentitol Inhibitors of GBA1 and GBA2
Gu, Xingxian,Gupta, Vijayalaxmi,Yang, Yan,Zhu, Jin-Yi,Carlson, Erick J.,Kingsley, Carolyn,Tash, Joseph S.,Sch?nbrunn, Ernst,Hawkinson, Jon,Georg, Gunda I.
, p. 1977 - 1984 (2017/11/30)
Analogues of N-butyl-1-deoxynojirimycin (NB-DNJ) were prepared and assayed for inhibition of ceramide-specific glucosyltransferase (CGT), non-lysosomal β-glucosidase 2 (GBA2) and the lysosomal β-glucosidase 1 (GBA1). Compounds 5 a–6 f, which carry sterically demanding nitrogen substituents, and compound 13, devoid of the C3 and C5 hydroxy groups present in DNJ/NB-DGJ (N-butyldeoxygalactojirimycin) showed no inhibitory activity for CGT or GBA2. Inversion of stereochemistry at C4 of N-(n-butyl)- and N-(n-nonyl)-DGJ (compounds 24) also led to a loss of activity in these assays. The aminocyclopentitols N-(n-butyl)- (35 a), N-(n-nonyl)-4-amino-5-(hydroxymethyl)cyclopentane- (35 b), and N-(1-(pentyloxy)methyl)adamantan-1-yl)-1,2,3-triol (35 f), were found to be selective inhibitors of GBA1 and GBA2 that did not inhibit CGT (>1 mm), with the exception of 35 f, which inhibited CGT with an IC50 value of 1 mm. The N-butyl analogue 35 a was 100-fold selective for inhibiting GBA1 over GBA2 (Ki values of 32 nm and 3.3 μm for GBA1 and GBA2, respectively). The N-nonyl analogue 35 b displayed a Ki value of ?14 nm for GBA1 inhibition and a Ki of 43 nm for GBA2. The N-(1-(pentyloxy)methyl)adamantan-1-yl) derivative 35 f had Ki values of ≈16 and 14 nm for GBA1 and GBA2, respectively. The related N-bis-substituted aminocyclopentitols were found to be significantly less potent inhibitors than their mono-substituted analogues. The aminocyclopentitol scaffold should hold promise for further inhibitor development.
Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-Addition/aldol reaction followed by RCM/syn-dihydroxylation
Malik, Micha?,Jarosz, S?awomir
supporting information, p. 2602 - 2608 (2017/01/09)
Synthesis of novel polyhydroxylated derivatives of decalin is described. The presented methodology consists in a one-pot copper-catalyzed 1,4-addition of vinylmagnesium bromide to sugar-derived cyclohexenone, followed by an aldol reaction with a derivativ
Stable analogues of nojirimycin-synthesis and biological evaluation of nojiristegine and manno-nojiristegine
Viuff, Agnete H.,Besenbacher, Louise M.,Kamori, Akiko,Jensen, Mikkel T.,Kilian, Mogens,Kato, Atsushi,Jensen, Henrik H.
, p. 9637 - 9658 (2015/09/28)
Two novel iminosugars called nojiristegines, being structural hybrids between nor-tropane alkaloid calystegine and nojirimycins, have been synthesised and found to be stable molecules despite the presence of a hemiaminal functionality. The synthesised iminosugars were evaluated against a panel of glycosidases and the best inhibition (IC50), found against α-glucosidases, was in the micromolar region. The compounds were also evaluated as potential antibiotics but no useful level of activity was observed.
Stereoselective and regioselective one-pot synthesis of polyhydroxy bicyclic diazenes and hydrazones from methyl 6-deoxy-6-iodo-hexosides
Li, Yunfeng,Meng, Yao,Li, Zhongjun,Meng, Xiangbao
, p. 5385 - 5390 (2015/07/15)
An efficient, stereoselective, and base-controlled procedure for the preparation of polyhydroxy bicyclic diazenes and polyhydroxy bicyclic hydrazones is described, starting from sugar-derived methyl 6-deoxy-6-iodo-hexosides. The one-pot synthesis involves
Synthesis and evaluation of eight- and four-membered iminosugar analogues as inhibitors of testicular ceramide-specific glucosyltransferase, testicular β-glucosidase 2, and other glycosidases
Lee, Jae Chul,Francis, Subhashree,Dutta, Dinah,Gupta, Vijayalaxmi,Yang, Yan,Zhu, Jin-Yi,Tash, Joseph S.,Schoenbrunn, Ernst,Georg, Gunda I.
, p. 3082 - 3098 (2012/05/31)
Eight- and four-membered analogues of N-butyldeoxynojirimycin (NB-DNJ), a reversible male contraceptive in mice, were prepared and tested. A chiral pool approach was used for the synthesis of the target compounds. Key steps for the synthesis of the eight-membered analogues involve ring-closing metathesis and Sharpless asymmetric dihydroxylation and for the four-membered analogues Sharpless epoxidation, epoxide ring-opening (azide), and Mitsunobu reaction to form the four-membered ring. (3S,4R,5S,6R,7R)-1-Nonylazocane-3,4,5,6,7-pentaol (6) was moderately active against rat-derived ceramide-specific glucosyltransferase, and four of the other eight-membered analogues were weakly active against rat-derived β-glucosidase 2. Among the four-membered analogues, ((2R,3S,4S)-3-hydroxy-1-nonylazetidine-2,4-diyl)dimethanol (25) displayed selective inhibitory activity against mouse-derived ceramide-specific glucosyltransferase and was about half as potent as NB-DNJ against the rat-derived enzyme. ((2S,4S)-3-Hydroxy-1-nonylazetidine-2,4-diyl)dimethanol (27) was found to be a selective inhibitor of β-glucosidase 2, with potency similar to NB-DNJ. Additional glycosidase assays were performed to identify potential other therapeutic applications. The eight-membered iminosugars exhibited specificity for almond-derived β-glucosidase, and the 1-nonylazetidine 25 inhibited α-glucosidase (Saccharomyces cerevisiae) with an IC50 of 600 nM and β-glucosidase (almond) with an IC50 of 20 μM. Only N-nonyl derivatives were active, emphasizing the importance of a long lipophilic side chain for inhibitory activity of the analogues studied.
Stereoselective synthesis of polyoxygenated linear diaza-triquinanes via intramolecular 1,3-dipolar cycloaddition of sugar-derived hex-5-enals
Li, Yunfeng,Meng, Yao,Meng, Xiangbao,Li, Zhongjun
experimental part, p. 4002 - 4008 (2011/06/25)
An efficient and stereoselective synthesis of diaza-triquinanes, the skeleton structures of many natural products, has been accomplished by intramolecular 1,3-dipolar cycloaddition of azomethine imine generated from sugar-derived hex-5-enal and pyrazolidi
