1-deoxy-2,3,4,6-tetra-O-acetyl-1-(2-cyanoethyl)-β-D-glucopyranose | 114644-71-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-deoxy-2,3,4,6-tetra-O-acetyl-1-(2-cyanoethyl)-β-D-glucopyranose
• 英文别名: 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)propionitrile；5,6,7,9-tetraacetate 4,8-anhydro-2,3-dideoxy-D-glycero-D-ido-nonononitrile；5,6,7,9-tetra-O-acetyl-4,8-anhydro-2,3-dideoxy-D-glycero-D-gulo-nonononitrile；[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-(2-cyanoethyl)oxan-2-yl]methyl acetate
• CAS: 114644-71-2
• 化学式: C₁₇H₂₃NO₉
• 分子量: 385.371
• InChiKey: NOXLEHNRIYFCQH-DMRKSPOLSA-N

物化性质

• 沸点：
  479.4±35.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  丙烯腈 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 Ni(tmc)2(BF₄)2 锰 、 二苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-deoxy-2,3,4,6-tetra-O-acetyl-1-(2-cyanoethyl)-β-D-glucopyranose 、 3-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)propionitrile
  参考文献：
  名称：

  Readman; Marsden; Hodgson, Synlett, 2000, # 11, p. 1628 - 1630

  摘要：

  DOI：

文献信息

• Towards α- or β-d-C-glycosyl compounds by tin-catalyzed addition of glycosyl radicals to acrylonitrile and vinylphosphonate, and flexible reduction of tetra-O-acetyl-α-d-glucopyranosyl bromide with cyanoborohydride
  作者：Jean-Pierre Praly、Azin Salek Ardakani、Isabelle Bruyère、Chrystelle Marie-Luce、Bing Bing Qin

  DOI：10.1016/s0008-6215(02)00052-6

  日期：2002.10

  These conditions led to 2-(α- d -manno-, and galactopyranosyl)-ethylphosphonates in 68 and 76% yields. Similarly, radical addition of acetylated 1-bromo-β- d -glucopyranosyl chloride ( 2 ) to acrylonitrile or diethyl vinylphosphonate afforded mainly intermediate chlorides which, upon radical reduction with excess tri- n -butyltin hydride, afforded the corresponding β anomers (40 and 38%, respectively)

  摘要在催化量的氯化三正丁基锡和过量的氰基硼氢化钠（或四正丁基铵）存在下，将乙酰化的α-d-吡喃葡萄糖基溴化物（1）光诱导自由基加成到丙烯腈或乙烯基膦酸二乙酯中，可以高效制备α-构型的壬腈和2-（α-d-吡喃葡萄糖基）-乙基膦酸酯（产率分别为79％和70％）。这些条件导致产率为68％和76％的2-（α-d-甘露糖基和吡喃并吡喃糖基）-乙基膦酸酯。类似地，将乙酰化的1-溴-β-d-吡喃葡萄糖基氯（2）自由基加成到丙烯腈或乙烯基膦酸二乙酯中，主要得到中间体氯化物，在用过量的三正丁基锡氢化物进行自由基还原后，得到相应的β异构体（40和分别由38％的CC和CH键形成。立体控制依赖于d -glycopyranos-1-yl自由基的α-立体选择性猝灭。我们还发现，在叔丁醇中用过量的NaBH 3 CN进行1的紫外光辐照，可得到1,3,4,6-四-O-乙酰基-2-脱氧-α-d-阿拉伯糖-己吡喃糖（结晶后占65％
• Efficient stereoselective synthesis of α-C-glycopyranosides using 2,2′-azobis(2,4-dimethyl-4-methoxyvaleronitrile) [V-70]
  作者：Kentoku Gotanda、Masato Matsugi、Miki Suemura、Chiyo Ohira、Atsunori Sano、Masahisa Oka、Yasuyuki Kita

  DOI：10.1016/s0040-4020(99)00587-6

  日期：1999.8

  Efficient synthesis of alpha-C-glycopyranosides through a radical addition reaction using 2.2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile) [V-70] as an initiator under mild condition was developed. This method made it possible to completely control the stereocenter at the anomeric position and obtain only the alpha-anomer in high yield compared with AIBN, Et3B, and photo irradiation methods. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A highly stereoselective synthesis of α-linked C-glycopyranosides using 2,2′-azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (V-70)
  作者：Yasuyuki Kita、Kentoku Gotanda、Atsunori Sano、Masahisa Oka、Kenji Murata、Miki Suemura、Masato Matsugi

  DOI：10.1016/s0040-4039(97)10259-3

  日期：1997.12

  alpha-linked C-glycopyranosides were obtained effectively by the radical addition reaction using V-70, an effective radical initiator under mild conditions. (C) 1997 Elsevier Science Ltd.
• Synthesis of C-pento, -hexo-, and -heptulo-pyranosyl compounds via radical CC bond-formation reactions
  作者：Bernd Giese、Jacques Dupuis、Michael Leising、Marianne Nix、Hans Jörg Lindner

  DOI：10.1016/s0008-6215(00)90896-6

  日期：1987.12
• 1-DEOXY-2,3,4,6-TETRA-O-ACETYL-1-(2-CYANOETHYL)-a-D-GLUCOPYRANOSE
  作者：Giese, Bernd、Dupuis、Nix, Marianne

  DOI：10.15227/orgsyn.065.0236

  日期：——