(+)-hyacinthacine A6 | 479348-17-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (+)-hyacinthacine A6
• 英文别名: Hyacinthacine A6；(1S,2R,3R,5R,8R)-3-(hydroxymethyl)-5-methyl-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,2-diol
• CAS: 479348-17-9
• 化学式: C₉H₁₇NO₃
• 分子量: 187.239
• InChiKey: AGLLYYHKZWZSKX-GOFVFXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3aR,4S,6R,8aR,8bS)-4-{[dimethyl(phenyl)silyl]methyl}-6-methyl-2-phenylhexahydro-3aH-[1,3]dioxolo[4,5-a]pyrrolizine 在 盐酸 、 叔丁基过氧化氢 、 四丁基氟化铵 、 potassium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+)-hyacinthacine A6
  参考文献：
  名称：

  (+)-风信子A6和(+)-风信子A7的全合成

  摘要：

  (+)-Hyacinthacines A 6 和 A 7 是由常见的后期中间体合成的，通过二氯乙烯酮与手性烯醇醚的立体选择性 [2+2] 环加成反应以高收率制备。氨基腈化学的灵活性是该方法的核心。

  DOI：

  10.1055/s-0033-1340107

文献信息

• Flexible Strategy for the Synthesis of Pyrrolizidine Alkaloids
  作者：Timothy J. Donohoe、Rhian E. Thomas、Matthew D. Cheeseman、Caroline L. Rigby、Gurdip Bhalay、Ian D. Linney

  DOI：10.1021/ol801415d

  日期：2008.8.21

  A general strategy for the production of pyrrolizidine alkaloids is described, starting from intermediate (+)-9. The key features are diastereoselective dihydroxylation, inversion at the ring junction by hydroboration of an enamine, and ring closure to form the bicyclo ring system. This route is attractive because of its brevity and versatility; four natural products were prepared with differing stereochemistry

  从中间体（+）-9开始，描述了制备吡咯烷核生物碱的一般策略。主要特征是非对映选择性二羟基化，烯胺的氢硼化在环结处发生转化以及闭环形成双环系统。该路线之所以具有吸引力，是因为它的简洁性和多功能性。制备了四种具有不同立体化学和取代模式的天然产物。最后，这项工作允许分配2,3,7-triepiaustraline和hyacinthacine A 7的绝对立体化学。
• A New Synthetic Approach to (+)-Hyacinthacine A₁and the First Total Synthesis and Absolute Configuration Assignment of Naturally Occurring (+)-Hyacinthacine A₆
  作者：Isidoro Izquierdo、María T. Plaza、Juan A. Tamayo、Fernando Sánchez-Cantalejo

  DOI：10.1002/ejoc.200700820

  日期：2007.12

  Naturally occurring (1S,2R,3R,7aR)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine [(+)-hyacinthacine A1 (1)] and(1S,2R,3R,5R,7aR)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine [(+)-hyacinthacine A6 (2)] have been synthesized by Wittig's methodology using aldehyde 7, prepared from (2R,3S,4R,5R)-3,4-bis(benzyloxy)-2′-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine (3, partially protected

  天然存在的 (1S,2R,3R,7aR)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine [(+)-hyacinthacine A1 (1)] 和 (1S,2R,3R,5R,7aR)-1,2-dihydroxy -3-羟甲基-5-甲基吡咯里西啶 [(+)-hyacinthacine A6 (2)] 已通过 Wittig 的方法合成，使用醛 7，由 (2R,3S,4R,5R)-3,4-bis(benzyloxy)-制备2'-O-（叔丁基二苯基甲硅烷基）-2,5-双（羟甲基）吡咯烷（3，部分保护的 DALDP），作为同手性原料和适当的叶立德，得到相应的 α,β-不饱和酯 8 或酮9分别进行内酰胺化和还原胺化，得到相应的中间体pyrrolizidin-5-one 11和完全保护的吡咯里西啶14。化合物11和14分别很容易转化为上述风信子1和2。(© Wiley-VCH
• Total synthesis of natural (+)-hyacinthacine A6 and non-natural (+)-7a-epi-hyacinthacine A1 and (+)-5,7a-diepi-hyacinthacine A6
  作者：Isidoro Izquierdo、María T. Plaza、Juan A. Tamayo、Francisco Franco、Fernando Sánchez-Cantalejo

  DOI：10.1016/j.tet.2010.03.049

  日期：2010.5

  Naturally occurring (1S,2R,3R,5R,7aR)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine [(+)-hyacinthacine A(6), 2] together with unnatural (1S,2R,3R,7aS)-1,2-dihydroxy-3-hydroxy-methylpyrrolizidine [(+)-7a-epi-hyacinthacine A(1), 3] and (1S,2R,3R,5S,7aS)-1,2-dihydroxy-3-hydroxy-methyl-5-methylpyrrolizidine [(+)-5,7a-diepi-hyacinthacine A(6), 4] have been synthesized from a DALDP derivative [5, (2R,35,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-pyrrolidine], as the homochiral starting material. The synthetic process employed took advantages of Wittig methodology followed by internal lactamization, in the case of (+)-7a-epi-hyacinthacine A(1) (3), and reductive amination for (+)-hyacinthacine A(6) (2) and (+)-5,7a-diepi-hyacinthacine A(6) (4). (C) 2010 Elsevier Ltd. All rights reserved.
• 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.
• Total Synthesis of (+)-Hyacinthacine A6 and (+)-Hyacinthacine A7
  作者：Philippe Delair、Julien Smith、Anushree Kamath、Andrew Greene

  DOI：10.1055/s-0033-1340107

  日期：——

  (+)-Hyacinthacines A 6 and A 7 have been synthesized from a common, late-stage intermediate, prepared in high yield through stereoselective [2+2] cycloaddition of dichloroketene to a chiral enol ether. The flexibility of aminonitrile chemistry is central to the approach.

  (+)-Hyacinthacines A 6 和 A 7 是由常见的后期中间体合成的，通过二氯乙烯酮与手性烯醇醚的立体选择性 [2+2] 环加成反应以高收率制备。氨基腈化学的灵活性是该方法的核心。