(E)-1,2,3,4,9,10,11,12-tetra-O-isopropylidene-7,8-dideoxy-7,8-didehydro-D-arabino-D-galactododec-7-ene-1,5-pyranos-6-ulose | 1352346-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (E)-1,2,3,4,9,10,11,12-tetra-O-isopropylidene-7,8-dideoxy-7,8-didehydro-D-arabino-D-galactododec-7-ene-1,5-pyranos-6-ulose
• 英文别名: (E)-1,2:3,4:9,10:11,12-tetra-O-isopropylidene-7,8-dideoxy-7,8-didehydro-D-arabino-D-galactododec-7-en-1,5-pyranos-6-ulose
• CAS: 1352346-28-1
• 化学式: C₂₄H₃₆O₁₀
• 分子量: 484.544
• InChiKey: IRWSKUZBFUXFBG-KJPLATBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  100.14
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (E)-1,2,3,4,9,10,11,12-tetra-O-isopropylidene-7,8-dideoxy-7,8-didehydro-D-arabino-D-galactododec-7-ene-1,5-pyranos-6-ulose 在 咪唑 、 sodium periodate 、 四氧化锇 、 zinc(II) tetrahydroborate 、 18-冠醚-6 、 硫酸 、 四丁基氯化铵 、 水 、 silica gel 、 sodium hydride 、 potassium carbonate 、 N-甲基吗啉氧化物 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 、 叔丁醇 为溶剂， 反应 726.0h， 生成
  参考文献：
  名称：

  Synthesis of long-chain monosaccharides via the coupling of three ‘normal’ sugar units via Wittig type methodology: unusual removal of the benzyl group under basic conditions

  摘要：

  The reaction of diacetonogalactose phosphonate 6 with 2,3:4,5-di-O-isopropylidene-D-arabinose (7) afforded C-12-higher sugar enone with an E-geometry across the double bond, which was converted into the fully protected C-11-aldehyde 16. This compound was very unreactive and resistant toward the Wittig type and Tebbe reagents, but under PTC conditions, underwent a reaction with stabilized sugar phosphonate to afford C-18-enone 17. Very surprisingly unusual removal of the benzyl blocks under these conditions was observed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.001
• 作为产物：
  描述：

  dimethyl (1,2:3,4-di-O-isopropylidene-α-D-galacto-heptopyranos-6-ulos-7-yl)phosphonate 、 2,3-二氟-6-硝基苯胺 在 18-冠醚-6 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以98%的产率得到(E)-1,2,3,4,9,10,11,12-tetra-O-isopropylidene-7,8-dideoxy-7,8-didehydro-D-arabino-D-galactododec-7-ene-1,5-pyranos-6-ulose
  参考文献：
  名称：

  Synthesis of long-chain monosaccharides via the coupling of three ‘normal’ sugar units via Wittig type methodology: unusual removal of the benzyl group under basic conditions

  摘要：

  The reaction of diacetonogalactose phosphonate 6 with 2,3:4,5-di-O-isopropylidene-D-arabinose (7) afforded C-12-higher sugar enone with an E-geometry across the double bond, which was converted into the fully protected C-11-aldehyde 16. This compound was very unreactive and resistant toward the Wittig type and Tebbe reagents, but under PTC conditions, underwent a reaction with stabilized sugar phosphonate to afford C-18-enone 17. Very surprisingly unusual removal of the benzyl blocks under these conditions was observed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.001