2-C-(羟基甲基)-2,3:5,6-二-O-(1-甲基亚乙基)-D-塔洛糖酸GAMMA-内酯 | 864846-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-C-(羟基甲基)-2,3:5,6-二-O-(1-甲基亚乙基)-D-塔洛糖酸GAMMA-内酯
• 英文名称: 2,3:5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-talono-1,4-lactone
• 英文别名: 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-talono-1,4-lactone；(3aS,6S,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one
• CAS: 864846-17-3
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: MFSQZAFRNGCTLH-LWIGBJQBSA-N

物化性质

• 熔点：
  109-111 °C(Solv: ethyl ether (60-29-7); cyclohexane (110-82-7))
• 沸点：
  415.1±45.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-C-(羟基甲基)-2,3:5,6-二-O-(1-甲基亚乙基)-D-塔洛糖酸GAMMA-内酯 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 sodium azide 、 水 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 3-C-azidomethyl-2,3-O-isopropylidene-D-erythrose
  参考文献：
  名称：

  [EN] PYRROLIDINE IMINOSUGARS USED IN THE TREATMENT OF CYSTIC FIBROSIS
  [FR] IMINOSUCRES DE PYRROLIDINE UTILISÉS DANS LE TRAITEMENT DE LA MUCOVISCIDOSE

  摘要：

  化合物的化学式（I），其中：R1选自H；线性或支链、取代或未取代的烷基、烯基、炔基和芳基，其中可选的取代基可与一个或多个独立选择的基团取代，包括：-OH；-F；-Cl；-Br；-I；-NH2；烷基氨基；二烷基氨基；线性或支链烷基、烯基、炔基和芳基；芳基；杂环芳基；线性或支链烷氧基；芳氧基；芳基烷氧基；-(烷基)氧(烷基)；-CN；-NO2；-COOH；-COO(烷基)；-COO(芳基)；-C(O)NH(烷基)；-C(O)NH(芳基)；磺酰基；烷基磺酰基；芳基磺酰基；磺胺基；烷基磺胺基；烷基硫基；烷基磺酰胺；芳基磺酰胺；-NHNH2；和-NHOH；或其生物同位素，药用盐或衍生物，在囊性纤维化的治疗中有应用。

  公开号：

  WO2011086347A1
• 作为产物：
  描述：

  2-C-tert-butyldimethylsilyloxymethyl-2,3:5,6-di-O-isopropylidene-D-talono-1,4-lactone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以3.25 g的产率得到2-C-(羟基甲基)-2,3:5,6-二-O-(1-甲基亚乙基)-D-塔洛糖酸GAMMA-内酯
  参考文献：
  名称：

  酮糖上的Kiliani反应：D-塔格糖和D-阿斯卡糖的分支碳水化合物构造基团

  摘要：

  用氰化钠处理D-塔格糖和D-庚烷，得到支链糖内酯的混合物。在酸的存在下用丙酮萃取粗产物可直接获得支链碳水化合物二丙酮化物，这可能与新的Chirons一样有价值。在这两种情况下，主要的内酯产品（具有2,3-顺式-二醇关系的二烯二酮）可以从酮己糖中结晶出约40％至50％的收率。报道了一种将30g D-塔格糖转化为24g的2,3：5,6-二-O-异亚丙基-2- C-羟甲基-D-talono-1,4-内酯的实用程序。

  DOI：

  10.1016/j.tetlet.2005.06.030

文献信息

• Green syntheses of new 2-C-methyl aldohexoses and 5-C-methyl ketohexoses: d-tagatose-3-epimerase (DTE)—a promiscuous enzyme
  作者：Nigel A. Jones、Devendar Rao、Akihide Yoshihara、Pushpakiran Gullapalli、Kenji Morimoto、Goro Takata、Stuart J. Hunter、Mark R. Wormald、Raymond A. Dwek、Ken Izumori、George W.J. Fleet

  DOI：10.1016/j.tetasy.2008.07.034

  日期：2008.8

  The Kiliani synthesis oil the 4 readily accessible ketohexoses (D-fructose, D-tagatose, L-sorbose, D-psicose) allows access to 4 diastereomeric 2-C-methyl-aldohexoses (2-C-methyl-D-mannose, 2-C-methyl-D-talose, 2-C-methyl-L-gulose, 2-C-methyl-D-allose) and 4 diastereomeric 2-C-methyl-alditols (2-C-methyl-mannitol, 2-C-methyl-D-talitol, 2-C-methyl-L-gulitol, 2-C-methyl-D-allitol). Microbial oxidation of 2-C-methyl-D-mannitol and 2-C-metllyl-L-gulitol gave 5-C-methyl-D-fructose; Microbial oxidation of 2-C-methyl-D-talitol afforded 5-C-methyl-D-psicose, whereas 2-C-methyl-D-allitol formed 5-C-methyl-Lpsicose. Both enantiomers of 5-C-methyl-fructose were equilibrated by D-tagatose-3-epimerase (DTE) with both enantiomers of 5-C-methyl-psicose. These transformations demonstrate that polyol dehydrogenases and DTE act on branched synthetic sugars. Full NMR analyses show that 5-C-methyl-D-fructose is present as the P-pyranose and P-furanose forms in a ratio of 90:10; all pyranose and furanose forms of 5-C-methyl-D-psicose are present in solution. The combination of chemical and biological procedures allows the environmentally friendly generation of a new family of branched monosaccharides. (C) 2008 Elsevier Ltd. All rights reserved.
• Cystic fibrosis and diabetes: isoLAB and isoDAB, enantiomeric carbon-branched pyrrolidine iminosugars
  作者：Daniel Best、Sarah F. Jenkinson、A. Waldo Saville、Dominic S. Alonzi、Mark R. Wormald、Terry D. Butters、Caroline Norez、Frederic Becq、Yves Blériot、Isao Adachi、Atsushi Kato、George W.J. Fleet

  DOI：10.1016/j.tetlet.2010.05.131

  日期：2010.8

  Acetonides are the only protecting groups used in the syntheses of isoDAB from D-ribose and of isoLAB from D-tagatose. isoDAB is a potent and highly specific competitive a-glucosidase inhibitor (for rice alpha-glucosidase, K(i) = 4 mu M for isoDAB compared to K(i) 14 mu M for DAB). isoDAB is not an whereas DAB is a potent inhibitor of glycogen phosphorylase. This is the first example of any potent inhibition of glycosidases by a carbon-branched iminosugar pyrrolidine. Although isoLAB shows no inhibition of any glycosidase, preliminary experiments suggest that isoLAB partially rescues the defective F508del-CFTR function and so may have a role in the study of cystic fibrosis. (C) 2010 Elsevier Ltd. All rights reserved.
• Kiliani reactions on ketoses: branched carbohydrate building blocks from D-tagatose and D-psicose
  作者：Raquel Soengas、Ken Izumori、Michela Iezzi Simone、David J. Watkin、Ulla P. Skytte、Wim Soetaert、George W.J. Fleet

  DOI：10.1016/j.tetlet.2005.06.030

  日期：2005.8

  D-Tagatose and D-psicose on treatment with sodium cyanide gave mixtures of branched sugar lactones; extraction of the crude products by acetone in the presence of acid permits direct access to branched carbohydrate diacetonides, likely to be of value as new chirons. In both cases, the major lactone products—diacetonides with a 2,3-cis-diol relationship—can be crystallised in around 40–50% yield from

  用氰化钠处理D-塔格糖和D-庚烷，得到支链糖内酯的混合物。在酸的存在下用丙酮萃取粗产物可直接获得支链碳水化合物二丙酮化物，这可能与新的Chirons一样有价值。在这两种情况下，主要的内酯产品（具有2,3-顺式-二醇关系的二烯二酮）可以从酮己糖中结晶出约40％至50％的收率。报道了一种将30g D-塔格糖转化为24g的2,3：5,6-二-O-异亚丙基-2- C-羟甲基-D-talono-1,4-内酯的实用程序。
• [EN] PYRROLIDINE IMINOSUGARS USED IN THE TREATMENT OF CYSTIC FIBROSIS<br/>[FR] IMINOSUCRES DE PYRROLIDINE UTILISÉS DANS LE TRAITEMENT DE LA MUCOVISCIDOSE
  申请人：SUMMIT CORP PLC

  公开号：WO2011086347A1

  公开（公告）日：2011-07-21

  A compound of formula (I) wherein: R1 is selected from H; linear or branched, substituted or unsubstituted alkyl, alkenyl, alkynyl and aralkyl and wherein the optional substitution may be with one or more groups independently selected from: -OH; -F; -Cl; -Br; -I; -NH2; alkylamino; dialkylamino; linear or branched alkyl, alkenyl, alkynyl and aralkyl; aryl; heteroaryl; linear or branched alkoxy; aryloxy; aralkoxy; -(alkylene)oxy(alkyl); -CN; -NO2; - COOH; -COO(alkyl); -COO(aryl); -C(O)NH(alkyl); -C(O)NH(aryl); sulfonyl; alkylsulfonyl; arylsulfonyl; sulfamoyl; alkylsulfamoyl; alkylthio; alkylsulfonamide; arylsulfonamide; -NHNH2; and -NHOH; or a bioisostere, pharmaceutically acceptable salt or derivative thereof, finds application in the treatment of cystic fibrosis.

  化合物的化学式（I），其中：R1选自H；线性或支链、取代或未取代的烷基、烯基、炔基和芳基，其中可选的取代基可与一个或多个独立选择的基团取代，包括：-OH；-F；-Cl；-Br；-I；-NH2；烷基氨基；二烷基氨基；线性或支链烷基、烯基、炔基和芳基；芳基；杂环芳基；线性或支链烷氧基；芳氧基；芳基烷氧基；-(烷基)氧(烷基)；-CN；-NO2；-COOH；-COO(烷基)；-COO(芳基)；-C(O)NH(烷基)；-C(O)NH(芳基)；磺酰基；烷基磺酰基；芳基磺酰基；磺胺基；烷基磺胺基；烷基硫基；烷基磺酰胺；芳基磺酰胺；-NHNH2；和-NHOH；或其生物同位素，药用盐或衍生物，在囊性纤维化的治疗中有应用。