2,3-isopropylidenedioxy-D-mannono-γ-lactone | 126354-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-isopropylidenedioxy-D-mannono-γ-lactone
• 英文别名: 2,3-O-isopropylidene-D-mannofuranose lactone；2,3-O-Isopropylidene-D-mannono-1,4-lactone；2,3-O-isopropylidene-L-gulono-1,4-lactone；(3aS,6R,6aS)-6-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 126354-67-4
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: SSSBRIPVSPUGBC-JWXFUTCRSA-N

物化性质

• 熔点：
  131-132 °C
• 沸点：
  429.2±45.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-isopropylidenedioxy-D-mannono-γ-lactone 在 吡啶 、 咪唑 、 Amberlite 120-(H+) 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 L-铝离子-1,4-内酯
  参考文献：
  名称：

  An efficient synthesis of l-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-d-mannono-1,4-lactone

  摘要：

  We reported herein an efficient synthesis of L-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-D-inannono-1,4-lactone in five steps. The key feature of this method involved a one-pot, 6 double inversion' procedure at the stereocenters of C-4 and C-5 Of D-mannono- 1,4-lactone to afford the target molecule. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.113
• 作为产物：
  描述：

  D-甘露糖-1,4-内酯 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 2,3-isopropylidenedioxy-D-mannono-γ-lactone
  参考文献：
  名称：

  Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-d-glucitol)

  摘要：

  Syntheses of 1,6-dideoxy-1,6-imino-D-mannitol (D-mannoazepane) (1) and 1,6-dideoxy-1,6-imino-D-glucitol (D-glucoazepane) (3) from D-isoascorbic acid and D-glucono-1,5-lactone, respectively, are described. The key step in both routes involved reductive aminative 1,6-cyclization with retention of configurations to give the corresponding lactams, which were subsequently reduced to afford compounds 1 and 3 in 24 and 28.5%, overall yield, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00757-3

文献信息

• Chiron approach for the synthesis of (5RS)-Hagen’s gland lactones from diacetone-d-mannose
  作者：Geetha Banda、I.E. Chakravarthy

  DOI：10.1016/j.tetasy.2006.06.012

  日期：2006.7

  A new and convergent synthetic route for (5RS)-Hagen’s lactones 1–4 is described, starting from bisacetonide mannofuranolactone 5. The key transformations in the synthesis are SmI2 mediated α-deoxygenation of a aldonolactone to 2-deoxy lactone, Pd(II) mediated oxidative cyclization and an oxidation of tetrahydrofuran to a furanone.

  为一个新的和会聚的合成路线（5个RS）-Hagen的内酯1 - 4中描述了从二缩丙酮mannofuranolactone开始5。合成过程中的关键转变是SmI 2介导的醛糖内酯的α-脱氧为2-脱氧内酯，Pd（II）介导的氧化环化和四氢呋喃的氧化为呋喃酮。
• Combinatorial library approach to iminocyclitols with biological activity
  申请人：Moriarity M. Robert

  公开号：US20070088164A1

  公开（公告）日：2007-04-19

  A method of synthesizing stereochemically defined iminocyclitol comprises replacing an intraring oxygen in a cyclic sugar by an intraring imine to form an iminocyclitol, wherein said iminocyclitol has a defined stereochemical configuration different from a stereochemical configuration of the cyclic sugar. The invention also provides combinatorial libraries of iminocyclitol compounds, allowing for diverse C1 and N-substitution. In addition, provided are methods of treating viral infections with iminocyclitols compounds.

  合成立体化定义的亚胺环糖醇的方法包括通过在环糖中替换环内氧原子为环内亚胺来形成亚胺环糖醇，其中所述亚胺环糖醇具有与环糖不同的定义的立体化配置。该发明还提供了亚胺环糖醇化合物的组合库，允许多样的C1和N取代。此外，还提供了使用亚胺环糖醇化合物治疗病毒感染的方法。
• Fucosidase inhibitor
  申请人：MONSANTO COMPANY

  公开号：EP0409812A2

  公开（公告）日：1991-01-23

  The synthesis of the novel fucosidase inhibitor, 2,6-imino-2,6,7-trideoxy-D-glycero-D-­gluco heptitol, is disclosed.

  本研究公开了新型岩藻糖苷酶抑制剂 2,6-亚氨基-2,6,7-三脱氧-D-甘油-D-葡萄糖庚醇的合成方法。
• Hudlicky, Tomas; Mandel, Martin; Rouden, Jacques, Journal of the Chemical Society. Perkin transactions I, 1994, # 12, p. 1553 - 1568
  作者：Hudlicky, Tomas、Mandel, Martin、Rouden, Jacques、Lee, Robert S.、Bachmann, Bryan、et al.

  DOI：——

  日期：——
• 2,3,4-Tri-O-acetyl-1,6-anhydro-β-d-mannopyranose, an artifact produced during carbohydrate analysis. A total synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-d-mannofuranose
  作者：Sukumar Manna、Bill H. McAnalley、Herman L. Ammon

  DOI：10.1016/0008-6215(93)84078-k

  日期：1993.4

  This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-beta-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-beta-D-mannofuranose is also described, and a novel dimer, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-5,5'-di-O-(1-methoxyethyl)-di-alpha-D-mannofuranose, has been isolated. The structure of the dimer is confirmed by X-ray analysis of a derivative, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-di-alpha-D-mannofuranose.