(1R,2S,3R,5R)-8-氮杂二环[3.2.1]辛烷-1,2,3-三醇 | 131580-36-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 中文名称: (1R,2S,3R,5R)-8-氮杂二环[3.2.1]辛烷-1,2,3-三醇
• 英文名称: calystegine A3
• 英文别名: calystegin A₃；(1R,2S,3R,5R)-8-azabicyclo[3.2.1]octane-1,2,3-triol
• CAS: 131580-36-4
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: XOCBOVUINUHZJA-MVIOUDGNSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  11
• 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：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3R,5R)-5-[(benzyl)(benzyloxycarbonyl)amino]-2,3-bis(benzyloxy)cycloheptanone 在 20 % Pd(OH)2/C 、 氢气 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 47.0h， 以84%的产率得到(1R,2S,3R,5R)-8-氮杂二环[3.2.1]辛烷-1,2,3-三醇
  参考文献：
  名称：

  以葡萄糖为原料的闭环复分解合成卡司新碱A3

  摘要：

  描述了从 D-葡萄糖合成去甲托烷生物碱 calystegine A3。关键步骤采用锌介导的串联反应，其中苄基保护的甲基 6-碘糖苷被裂解成不饱和醛，然后将其转化为相应的苄亚胺并在同一个锅中烯丙基化。通过闭环烯烃复分解，由此获得的官能化的九-1,8-二烯被转化为calystegine A3中的七元碳骨架。随后通过 Barton-McCombie 方案进行脱氧、硼氢化和氧化后处理，然后氢解得到 calystegine A3。该合成总共使用了 13 个葡萄糖步骤，并确认了天然产物的绝对构型。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900310

文献信息

• Chiral pool synthesis of calystegine A3 from 2-deoxyglucose via a Brown allylation
  作者：Tina Secher Rasmussen、Henrik Helligsø Jensen

  DOI：10.1016/j.carres.2011.10.025

  日期：2011.12

  Calystegine A(3) is a naturally occurring nortropane iminosugar of which there previously have been three total syntheses. Inspired by our previous work we here report on a fourth approach using 17 steps from 2-deoxy-D-glucose applying a diastereoselective allylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.
• TREATMENT OF PROTEIN FOLDING DISORDERS
  申请人：Kawamura Akane

  公开号：US20100317690A1

  公开（公告）日：2010-12-16

  Described are various compounds and methods for the treatment of disorders arising from aberrant protein folding, including in particular lysosomal storage diseases. In particular, polyhydroxylated alkaloids and imino sugars which are pharmacoperones of an enzyme and which do not bind to a catalytic site of said enzyme are described.
• TREATMENT OF LYSOSOMAL STORAGE DISORDERS AND OTHER PROTEOSTATIC DISEASES
  申请人：De Moor Olivier

  公开号：US20110237538A1

  公开（公告）日：2011-09-29

  Described are various compounds, in particular iminosugars, and methods for the treatment of proteostatic diseases, in particular lysosomal storage disorders. The compound may be a pharmacoperone of an enzyme selected from: (a) Acid alpha-glucosidase; (b) Acid beta-glucosidase; (c) glucocerebrosidase; (d) alpha-Galactosidase A; (e) Acid beta-galactosidase; (f) beta-Hexosaminidase A; (g) beta-Hexosaminidase B; (h) Acid sphingomyelinase; (i) Galactocerebrosidase; (j) Acid ceramidase; (k) Arylsulfatase A; (l) alpha-L-Iduronidase; (m) Iduronate-2-sulfatase; (n) Heparan N-sulfatase; (o) alpha-N-Acetylglucosaminidase; (p) Acetyl-CoA: alpha-glucosaminide N-acetyltransferase; (q) N-Acetylglucosamine-6-sulfate sulfatase; (r) N-Acetylgalactosamine-6-sulfate sulfatase; (s) Acid beta-galactosidase; (t) Arylsulfatase B; (u) beta-Glucuronidase; (v) Acid alpha-mannosidase; (w) Acid beta-mannosidase; (x) Acid alpha-L-fucosidase; (y) Sialidase; and (z) alpha-N-acetylgalactosaminidase.
• Synthesis of Calystegine A₃from Glucose by the Use of Ring-Closing Metathesis
  作者：Rune Nygaard Monrad、Charlotte Bressen Pipper、Robert Madsen

  DOI：10.1002/ejoc.200900310

  日期：2009.7

  seven-membered carbon skeleton in calystegine A3 by ring-closing olefin metathesis. Subsequent deoxygenation by the Barton–McCombie protocol, hydroboration and oxidative workup followed by hydrogenolysis affords calystegine A3. The synthesis uses a total of 13 steps from glucose and confirms the absolute configuration of the natural product.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany,

  描述了从 D-葡萄糖合成去甲托烷生物碱 calystegine A3。关键步骤采用锌介导的串联反应，其中苄基保护的甲基 6-碘糖苷被裂解成不饱和醛，然后将其转化为相应的苄亚胺并在同一个锅中烯丙基化。通过闭环烯烃复分解，由此获得的官能化的九-1,8-二烯被转化为calystegine A3中的七元碳骨架。随后通过 Barton-McCombie 方案进行脱氧、硼氢化和氧化后处理，然后氢解得到 calystegine A3。该合成总共使用了 13 个葡萄糖步骤，并确认了天然产物的绝对构型。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)