Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars

Tilekar JN.; Patil NT.; Jadhav HS.; Dhavale DD.

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Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars

机译：简便实用的（2S，3R，4R，5R）和（2S，3R，4R，5S）-1,6-dideoxy-1,6-iminosugar的合成

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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 by intramolecular reductive amination of amino-aldehyde. (C) 2003 Published by Elsevier Science Ltd. [References: 30]

机译：描述了分别由D-葡萄糖合成（2S，3R，4R，5R）和（2S，3R，4R，5S）-1，6-二脱氧-1，6亚氨基糖1a和1b。该反应序列中的关键转化包括用N-苄基胺进行的区域选择性环氧化物开环，然后进行氨基醛的分子内还原胺化。（C）2003年由Elsevier Science Ltd.发布。[参考：30]

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《Tetrahedron》 |2003年第11期|共4页
作者
Tilekar JN.; Patil NT.; Jadhav HS.; Dhavale DD.;
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正文语种 eng
中图分类有机化学;
关键词
Carbohydrates; Imino sugars; Enzyme inhibitors; D-glucoazepane; L-idoazepane; Polyhydroxylated azepanes; Glycosidase inhibitors; Organic-synthesis; Sugar; Analogs; 1-deoxy-8a-epi-castanospermine; 1-deoxy-castanospermine; Selectivity; Azasugars;

机译：碳水化合物;氨基糖;酶抑制剂;D-葡萄糖氮庚烷;L-氨基氮杂庚烷;多羟基化的沸腾石棉;糖苷酶抑制剂;有机合成;糖;类似物;1-脱氧-8a-表-castanospermine;1-deoxy-castanospermine;选择性;Azasugars;

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专利

1. Convenient synthesis of (2S,3R,4R,5S,6R)-2-(3-(4-ethylbenzyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol [J] . Yong Hai Liu, Da Li Li, Lu De Lu, 中国化学快报（英文版） . 2008,第007期
2. Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars [J] . Tilekar JN., Patil NT., Jadhav HS., Tetrahedron . 2003,第11期

机译：简便实用的（2S，3R，4R，5R）和（2S，3R，4R，5S）-1,6-dideoxy-1,6-iminosugar的合成
3. (2S,3R,4R,5R)-3,4-Dihydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid [(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)proline] [J] . Best D., Fleet G.W.J., Jenkinson S.F., Acta Crystallographica Section E: Crystallographic Communications . 2009,第10期

机译：（2S，3R，4R，5R）-3,4-二羟基-5-（羟甲基）吡咯烷-2-羧酸[（2S，3R，4R，5R）-3,4-二羟基-5-（羟甲基）脯氨酸]
4. Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl) piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2 [J] . Simone M.I., Soengas R.G., Jenkinson S.F., Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2012,第5期

机译：三种支链亚氨基糖[（3R，4R，5S）-3-（羟甲基）哌啶-3,4,5-三醇，（3R，4R，5R）-3-（羟甲基）哌啶-3,4,5-的合成三醇和（3S，4R，5R）-3-（羟甲基）哌啶-3,4,5-三醇]和支链三羟基己酸[（3R，4R，5R）-3,4,5-三羟基哌啶-3-羧酸酸]的糖内酯在C-2处有一个碳取代基
5. On-chip detection of wild 3R, 4R and mutant 4R tau through kinesin-microtubule binding [C] . Subramaniyan S.P., Tarhan M.C., Karsten S.L., IEEE International Conference on Micro Electro Mechanical Systems . 2015

机译：通过驱动蛋白-微管结合对野生型3R，4R和突变型4R tau进行芯片检测
6. (3R,4S),(3S,4R) and (3R,4R),(3S,4S)-4-amino-5-fluoro-3-phenyl pentanoic acids as mechanism-based inactivators of 4-aminobutyric acid aminotransferase [D] . Nanavati, Shrenik M. 1988

机译：（3R，4S），（3S，4R）和（3R，4R），（3S，4S）-4-氨基-5-氟-3-苯基戊酸是基于机制的4-氨基丁酸氨基转移酶灭活剂
7. (3R,4R,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one [O] . Annika Gille, Markus Schürmann, Hans Preut, 2016

机译：（3R，4R，5S）-4-羟基-3-甲基-5-[（2S，3R）-3-甲基戊-4-烯-2-基] -4,5-二氢呋喃-2（3H）-
8. (2S,3R,4R,5R)-3,4-Dihydr-oxy-5-(hydroxy-meth-yl)pyrrolidine-2-carboxylic acid [(2S,3R,4R,5R)-3,4-dihydr-oxy-5-(hydroxy-meth-yl)proline]. [O] . Best, D, Jenkinson, SF, Thompson, AL, 2009

机译：（2S，3R，4R，5R）-3,4-二氢氧基-5-（羟基-甲基-甲基）吡咯烷-2-羧酸[（2S，3R，4R，5R）-3,4-二氢-氧-5-（羟甲基）脯氨酸]。

Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars

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