tert-butyl 2-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-3,6-furanoso-3-octulosonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 2-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-3,6-furanoso-3-octulosonate
• 英文别名: tert-butyl 2-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetate
• 化学式: C₁₈H₃₀O₈
• 分子量: 374.431
• InChiKey: FKWMIHRGVXZUPB-WOIDLZKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 在 molecular sieve 、 magnesium 、 pyridinium chlorochromate 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 tert-butyl 2-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-3,6-furanoso-3-octulosonate
  参考文献：
  名称：

  A new Co(0) complex mediated synthesis of C-glycoside analogues

  摘要：

  Properly protected glyconolactones, readily available from the parent sugars, react under mild conditions with alpha-bromoacetates in the presence of a soluble Co(0) complex, either in stoichiometric Or substoichiometric amounts, to give a Reformatsky-type addition product to the lactone. The addition product can be Subsequently converted into a variety of compounds: dehydroxylation with triethylsilane in the presence of boron trifluoride affords C-glycosides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00533-0

文献信息

• Stereoselective synthesis of α-substituted ulosonic acids by magnesio-reformatsky reactions
  作者：René Csuk、Christina Schröder、Claus Krieger

  DOI：10.1016/s0040-4020(97)00813-2

  日期：1997.9

  A new method of homologation of aldonolactones allowing the incorporation of propionate units with excellent chemo- and stereoselectivity is performed by the magnesium-graphite mediated reaction between Oppolzer sultam derived α-halogenated amides and an aldonolactone.

  Oppolzer sultam衍生的α-卤代酰胺与Aldonolactone之间的镁-石墨介导的反应，是一种使Aldonolactones同源化的新方法，该方法可以使丙酸酯单元具有出色的化学和立体选择性。
• Synthesis of α-substituted 3-ulosonic acids from aldonolactones
  作者：René Csuk、Ulrike Franke (nee Höring)、Zhong Hu、Claus Krieger

  DOI：10.1016/j.tet.2003.08.014

  日期：2003.9

  Zinc–silver/graphite mediated Reformatsky-reaction of furanoid aldonolactones with α-bromo-esters allows the synthesis of α-substituted 3-ulosonic acids in high yields.

  锌-银/石墨介导的呋喃类阿糖内酯与α-溴代酸酯的Reformatsky反应可合成高产率的α-取代的3-磺酸。
• A new Co(0) complex mediated synthesis of C-glycoside analogues
  作者：Fulvia Orsini、Emanuela Di Teodoro

  DOI：10.1016/s0957-4166(03)00533-0

  日期：2003.9

  Properly protected glyconolactones, readily available from the parent sugars, react under mild conditions with alpha-bromoacetates in the presence of a soluble Co(0) complex, either in stoichiometric Or substoichiometric amounts, to give a Reformatsky-type addition product to the lactone. The addition product can be Subsequently converted into a variety of compounds: dehydroxylation with triethylsilane in the presence of boron trifluoride affords C-glycosides. (C) 2003 Elsevier Ltd. All rights reserved.