- Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction
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The Henry reaction with the easily available α-d-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the α-d-gluco- and β-l-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the α
- Chakraborty, Chaitali,Dhavale, Dilip D.
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- Concise and practical route to tri- and tetra-hydroxy seven-membered iminocyclitols as glycosidase inhibitors from d-(+)-glucurono-γ-lactone
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An efficient and short total synthesis of tetrahydroxy-1c and trihydroxy-azepane 1d is reported in 72% and 57% overall yields, respectively, from d-(+)-glucurono-γ-lactone. Thus, d-glucuronolactone 2 on acetonide protection, DIBAL-H reduction and one-pot intermolecular reductive amination followed by -NCbz protection afforded 6-(N-benzyl-N-benzyloxycarbonyl) amino-6-deoxy-1,2-O-isopropylidene-α-d-gluco-1,4-furanose 5a. 1,2-Acetonide hydrolysis in 5a and Pd-mediated intramolecular reductive aminocyclization afforded tetrahydroxyazepane 1c. An analogous pathway with 5-deoxy-1,2-O-isopropylidene-α-d-glucurono-6,3-lactone 3b gave trihydroxy-azepane 1d. Glycosidase inhibitory activity of 1c/1d was studied and 1d was found to be potent inhibitor of α-mannosidase and β-galactosidase.
- Kalamkar, Navnath B.,Kasture, Vijay M.,Chavan, Sanjay T.,Sabharwal, Sushma G.,Dhavale, Dilip D.
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experimental part
p. 8522 - 8526
(2010/11/18)
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- Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars
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The syntheses of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6 iminosugars 1a and 1b, respectively, from D-glucose are described. The key transformations in this reaction sequence include regio-selective epoxide ring opening with N-benzylamine followed
- Tilekar, Jayant N.,Patil, Nitin T.,Jadhav, Harishchandra S.,Dhavale, Dilip D.
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p. 1873 - 1876
(2007/10/03)
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- An easy route to seven-membered iminocyclitols from aldohexopyranosyl enamines
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A new stereocontrolled and high yielding synthesis of biologically active polyhydroxyperhydroazepines is reported starting from easily available glycosylenamines (D-gluco, D-manno, and D-galacto configurations), which are transformed into 1,6-azaanhydropy
- Fuentes, Jose,Gasch, Consolacion,Olano, David,Pradera,Repetto, Guillermo,Sayago, Francisco J.
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p. 1743 - 1753
(2007/10/03)
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- Seven-membered ring azasugars as glycosidase inhibitors and anticancer agents
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Synthesis of various C2 symmetrical tetrahydroxyazepanes has been reported by the reaction of bisepoxides with various primary, amines. The tetrahydroxyazepanes inhibit β-glucosidases in micromolar range and also exhibit anticancer activity in
- Lohray,Bhushan, Vidya,Prasuna,Jayamma,Raheem,Papireddy,Umadevi,Premkumar,Lakshmi,Narayanareddy
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p. 1311 - 1321
(2007/10/03)
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- Synthesis of new N-containing maltooligosaccharides, α-amylase inhibitors, and their biological activities
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Fifteen new N-containing maltooligosaccharides were obtained using the chemoenzymatic method. Among these compounds, maltooligosaccharides having 6- amino-6-deoxy-D-sorbitol residue, (3R,4R,5R,6S)-hexahydro-3,4,5,6- tetrahydroxy-1H-azepine residue, and (3R,5R)-3,4,5-trihydroxypiperidine residue at the reducing end showed strong inhibitory activities for human pancreatic α-amylase (HPA) (EC 3.2.1.1) and human salivary amylase (HSA). The administration of (3R,4R,5R,6S)-hexahydro-3,5,6-trihydroxy-1H-azepine-4- yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (13, IC50=4.3x10-5M for HPA, IC50=8.2x10-5M for HSA) and (3R,5R)-3,5-dihydroxypiperidine-4- yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (18, IC50=3.4x10-5M for HPA, IC50=4.6 x 10-5 M for HSA) to ICR mice suppressed postprandial hyperglycemia.
- Uchida, Riichiro,Nasu, Ayako,Tokutake, Shoichi,Kasai, Kouichi,Tobe, Koichiro,Yamaji, Nobuyuki
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p. 187 - 193
(2007/10/03)
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- Enzymatic/chemical synthesis and biological evaluation of seven-membered iminocyclitols
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Several polyhydroxyperhydroazepines have been obtained either by chemoenzymatic or chemical synthesis. Condensation of (±)-3-azido-2-hydroxypropanaldehyde and dihydroxyacetone phosphate (DHAP) in the presence of a DHAP dependent aldolase followed by treat
- Morís-Varas, Francisco,Qian, Xin-Hua,Wong, Chi-Huey
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p. 7647 - 7652
(2007/10/03)
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