6-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-5-O-(methylsulfonyl)-D-mannono-1,4-lactone | 677344-12-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-5-O-(methylsulfonyl)-D-mannono-1,4-lactone
• 英文别名: 5-O-methanesulfonyl-6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-mannono-1,4-lactone；[(1R)-1-[(3aS,6S,6aS)-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-6-yl]-2-[tert-butyl(dimethyl)silyl]oxyethyl] methanesulfonate
• CAS: 677344-12-6
• 化学式: C₁₆H₃₀O₈SSi
• 分子量: 410.561
• InChiKey: FBLZBXNVTANUGL-NDBYEHHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-5-O-(methylsulfonyl)-D-mannono-1,4-lactone 在 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：

  2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 吡啶 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-5-O-(methylsulfonyl)-D-mannono-1,4-lactone
  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

文献信息

• Synthesis and Oxidation ofN-Aminoglyconolactams: A Synthesis of Mannostatin A
  作者：Guixian Hu、Andrea Vasella

  DOI：10.1002/hlca.200490217

  日期：2004.9

  known methanesulfonate 2. Oxidation of 4 with t-BuOCl in the presence of 2,6-lutidine afforded the tetrazene 6 (63%). Oxidation with MnO2 gave the deaminated lactam 7 (40%), which was also obtained, together with the lactone 8, upon oxidation of 4 with PhSeO2H. Oxidation with Mn(OAc)3/Cu(OAc)2 provided the lactam 7 as the major and the dimer 9 as the minor product. Oxidation of 4 with 3 equiv. of Pb(OAc)4

  所述Ñ氨基核糖酸-1,5-内酰胺4以两个高产步骤制备从已知的甲磺酸酯2。在2，6-二甲基吡啶存在下，用t- BuOCl氧化4，得到四烯6（63％）。用MnO 2氧化得到脱氨基的内酰胺7（40％），当用PhSeO 2 H氧化4时，它也与内酯8一起获得。用Mn（OAc）3 / Cu（OAc）2氧化得到内酰胺7作为主要和二聚体9作为次要产品。4当量与3当量的氧化。在室温下，于甲苯中溶解Pb（OAc）4，得到两个环戊烷。乙酰氧基环氧化物10和重氮酮11的总产率为78％。氧化用PB（OBZ）4提供11和结晶苯甲酰氧基环氧化物12。通过X射线分析确定了12的晶体结构。所述Ñ氨基glyconolactams 41,46和51类似地制备到4。用Pb（OAc）4氧化可得到重氮酮56、57和58是唯一可隔离的产品。在DMSO存在下，用Pb（OAc）4氧化N-氨基甘露聚糖-1,5-内酰胺55，得到亚磺酰亚胺59
• 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。
• An efficient synthesis of l-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-d-mannono-1,4-lactone
  作者：Tzenge-Lien Shih、Jui-Huang Tseng

  DOI：10.1016/j.tetlet.2003.12.113

  日期：2004.2

  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.