(1R,6R,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetraol | 121250-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1R,6R,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetraol
• 英文别名: 1,6-diepicastanospermine；(1R,6R,7R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol
• CAS: 121250-62-2
• 化学式: C₈H₁₅NO₄
• 分子量: 189.211
• InChiKey: JDVVGAQPNNXQDW-FMDGEEDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-benzyl-4-O-benzyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol 在 草酰氯 、 甲烷磺酸 、 二甲基硫 、 硼烷 、 双氧水 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 反应 2.0h， 生成 (1R,6R,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetraol
  参考文献：
  名称：

  由L-古洛内酯合成6-表锡精胺和1,6-二甜基葡萄精胺和由D-古洛内酯合成L-6-表锡精胺和L-1,6-二甜基葡萄精胺

  摘要：

  天然产物6-表皮锡精胺[（1S，6R，7R，8R，8aR）-1,6,7,8-四羟基八氢吲哚嗪]和1,6-diepicastastspermine [（1R，6R L-古洛内酯中的1,7R，8R，8aR）-1,6,7,8-四羟基八氢-吲哚嗪和对映体L-6-表锡精胺[（1R，6S，7S，8S，8aS）-1据报道，来自D-古洛内酯的，6,7,8-四羟基八氢吲哚嗪]和L-1,6-二甲基甜精胺[（1S，6S，7S，8S，8aS）-1,6,7,8-四羟基八氢吲哚嗪]。

  DOI：

  10.1016/0040-4039(88)85305-x

文献信息

• A new and highly stereoselective synthesis of polyhydroxyindolizidines from 4-octulose derivatives
  作者：Isidoro Izquierdo、Maria T Plaza、Rafael Robles、Antonio J Mota

  DOI：10.1016/s0957-4166(98)00064-0

  日期：1998.3

  (1S,2S,6R,7R,8R,8aR)-1,2,6,7,8-Pentahydroxyindolizidine 12 and (1R,6R,7R,8R,8aR)-1,6,7,8-tetrahydroxyindolizidine (1,6-diepicastanospermine, 24) have been stereoselectively synthesized from the important key intermediates 1,4-dideoxy-1,4-imino-D-erythro-L-altro-octitol 7 and 1,2,4-trideoxy-1,4-imino-D-glycero-D-talo-octitol 20 in three steps. Compounds 7 and 20 were readily obtained from 2,3:4,5:6,7-tri-O-isopropylidene-beta-D-glycero-D-galacto-oct-4-ulo-4,8-pyranose 1 and 2-deoxy-4,5:6,7-di-O-isopropylidene-beta-D-manno-oct-4-ulo-4,8-pyranose 13 in four steps, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  (1S,2S,6R,7R,8R,8aR)-1,2,6,7,8-五羟基吲哚齐啶（12）和(1R,6R,7R,8R,8aR)-1,6,7,8-四羟基吲哚齐啶（1,6-去环化合欢啶，24）已从重要关键中间体1,4-去氧-1,4-亚胺基-D-赤-L-阿洛-octitol（7）和1,2,4-三去氧-1,4-亚胺基-D-甘露糖基-D-塔罗-octitol（20）中以三步法立体选择性地合成。化合物7和20分别以四步法从2,3:4,5:6,7-三-O-异丙叉基-D-甘露糖基-D-半乳糖-oct-4-ulo-4,8-吡喃糖（1）和2-deoxy-4,5:6,7-二-O-异丙叉基-D-甘露糖-oct-4-ulo-4,8-吡喃糖（13）中容易获得。版权：1998 Elsevier Science Ltd. 保留所有权利。
• Synthesis of the enantiomers of 6-epicastanospermine and 1,6-diepicastanospermine from d- and l-gulonolactone
  作者：George W.J. Fleet、Nigel G. Ramsden、Robert J. Nash、Linda E. Fellows、Gary S. Jacob、Russell J. Molyneux、Isabelle Cenci di Bello、Bryan Winchester

  DOI：10.1016/0008-6215(90)80146-t

  日期：1990.9

  The synthesis of the enantiomers of 6-epicastanospermine and of 1,6-diepicastanospermine from the enantiomeric gulonolactones is reported and the structure of the former is established as (1S,6R,7R,8R,8aR)-1,6,7,8-tetrahydroxyoctahydroindolizine. The inhibitory activities of the diastereomers against the amyloglucosidase-catalysed hydrolysis of p-nitrophenyl alpha-D-glucopyranoside were investigated

  据报道，由对映体古洛内酯合成6-表锡精胺和1,6-二硬脂精胺的对映异构体，前者的结构确定为（1S，6R，7R，8R，8aR）-1,6,7,8 -四羟基八氢吲哚嗪。研究了非对映异构体对淀粉葡糖苷酶催化的对硝基苯基α-D-葡萄糖吡喃糖苷水解的抑制活性，并报道了6-表二十碳四烯精胺和1,6-二甲基吡喃二精胺对14种人肝糖苷酶的影响。
• Synthesis of polyhydroxylated pyrrolizidine and indolizidine compounds and their glycosidase inhibitory activities
  作者：Thunwadee Ritthiwigrom、Robert J. Nash、Stephen G. Pyne

  DOI：10.1016/j.tet.2010.10.008

  日期：2010.11

  The synthesis of the natural product 3-epi-casuarine and two tricyclic ether bridged analogues, plus 7-deoxy-3,6-diepi-casuarine, 7-epi-australine, 1-epi-castanospermine and 1,6-diepi-castanospermine is described. The glycosidase inhibitory activities of these compounds, along with that of uniflorine A and other polyhydroxylated pyrrolizidines and indolizidines that we have published before, are reported

  天然产物3- Epi- casuarine和两个三环醚桥联的类似物，加上7-脱氧-3,6-di epi - casuarine，7- Epi- australine，1- epi -castanospermine和1,6-di epi的合成-castanospermine被描述。据报道，这些化合物的糖苷酶抑制活性，以及​​我们以前已发表的单花青素A和其他多羟基化的吡咯并核苷和吲哚并核苷的活性。
• Stereocontrolled syntheses of polyhydroxy indolizidines, including 8a-epi-, 6,8a-diepi- and 1,6-diepi-castanospermine, starting from malic acid
  作者：Finian J. Leeper、Steven Howard

  DOI：10.1016/0040-4039(95)00249-c

  日期：1995.3

  Stereocontrolled total syntheses of one trihydroxy indolizidine 15 and three tetrahydroxy indolizidines, 17, 21 and 23 - all diastereoisomers of castanospermine - are described which use malic acid as the only chiral starting material.
• An asymmetric synthesis of D-1,6-Diepicastanospermine
  作者：Keyin Burgess、David A. Chaplin

  DOI：10.1016/s0040-4039(00)60010-2

  日期：1992.10

  D-1,6-Diepicastanospemine has been prepared via reaction of an allylstannane with the arabinose derivative 1a. This reaction was almost 100 % stereoselective, but the corresponding allylations of aldehydes 1b - d gave mixtures of isomers. Variable stereodifferentiation in these reactions can be attributed to the influence of the distal (gamma) chiral center.