6-deoxy-6-N-benzyloxycarbonyl-1,2-O-isopropylidene-3-O-phenylmethyl-α-D-gluco-1,4-furanose | 551960-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-deoxy-6-N-benzyloxycarbonyl-1,2-O-isopropylidene-3-O-phenylmethyl-α-D-gluco-1,4-furanose
• 英文别名: 6-deoxy-6-N-benzyloxycarbonylamino-1,2-O-isopropylidene-α-D-gluco-1,4-furanose；benzyl N-[(2R)-2-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl]carbamate
• CAS: 551960-79-3
• 化学式: C₁₇H₂₃NO₇
• 分子量: 353.372
• InChiKey: XNWYSJTWHANUHO-XLWJZTARSA-N

物化性质

• 沸点：
  564.9±50.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-deoxy-6-N-benzyloxycarbonyl-1,2-O-isopropylidene-3-O-phenylmethyl-α-D-gluco-1,4-furanose 在 palladium on activated charcoal 三氟乙酸 、 氢气 作用下， 以 水 、 盐酸 、 甲醇 为溶剂， 25.0 ℃ 、551.58 kPa 条件下， 反应 26.5h， 以81%的产率得到(3R,4R,5R,6S)-hexahydro-3,4,5,6-tetrahydroxy-1H-azepine
  参考文献：
  名称：

  Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction

  摘要：

  The Henry reaction with the easily available alpha-D-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the alpha-D-gluco- and beta-L-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the alpha-D-gluco-nitroaldose as the only product. The reduction of the nitro group in the alpha-D-gluco- and beta-L-ido-nitroaldoses, removal of the protecting groups and intramolecular reductive cyclo-amination afforded the corresponding (2S,3R,4R,5R) and (2S,3R,4R,5S) tetrahydroxyazepanes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.007
• 作为产物：
  描述：

  5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 在 palladium on activated charcoal ammonium formate 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 14.67h， 生成 6-deoxy-6-N-benzyloxycarbonyl-1,2-O-isopropylidene-3-O-phenylmethyl-α-D-gluco-1,4-furanose
  参考文献：
  名称：

  Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars

  摘要：

  The syntheses of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6 iminosugars 1a and 1b, respectively, from D-glucose are described. The key transformations in this reaction sequence include regio-selective epoxide ring opening with N-benzylamine followed by intramolecular reductive amination of amino-aldehyde. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(03)00177-7

文献信息

• Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars
  作者：Jayant N Tilekar、Nitin T Patil、Harishchandra S Jadhav、Dilip D Dhavale

  DOI：10.1016/s0040-4020(03)00177-7

  日期：2003.3

  The syntheses of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6 iminosugars 1a and 1b, respectively, from D-glucose are described. The key transformations in this reaction sequence include regio-selective epoxide ring opening with N-benzylamine followed by intramolecular reductive amination of amino-aldehyde. (C) 2003 Published by Elsevier Science Ltd.
• Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction
  作者：Chaitali Chakraborty、Dilip D. Dhavale

  DOI：10.1016/j.carres.2006.02.007

  日期：2006.5

  The Henry reaction with the easily available alpha-D-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the alpha-D-gluco- and beta-L-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the alpha-D-gluco-nitroaldose as the only product. The reduction of the nitro group in the alpha-D-gluco- and beta-L-ido-nitroaldoses, removal of the protecting groups and intramolecular reductive cyclo-amination afforded the corresponding (2S,3R,4R,5R) and (2S,3R,4R,5S) tetrahydroxyazepanes. (c) 2006 Elsevier Ltd. All rights reserved.