(R,E)-3-((4S,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolan)]-5-yl)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)prop-2-en-1-ol | 1352346-29-2

• 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: (R,E)-3-((4S,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolan)]-5-yl)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)prop-2-en-1-ol
• CAS: 1352346-29-2
• 化学式: C₂₄H₃₈O₁₀
• 分子量: 486.56
• InChiKey: YPWVGHJINVOLGR-QRPWKKJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 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：
  0.92
• 拓扑面积：
  103.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (R,E)-3-((4S,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolan)]-5-yl)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)prop-2-en-1-ol 在 咪唑 、 四氧化锇 、 水 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 、 叔丁醇 为溶剂， 反应 240.5h， 生成 (1R,2R,3R)-3-(benzyloxy)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolan)]-5-yl)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)propane-1,2-diol
  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：

  (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 zinc(II) tetrahydroborate 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以96.7%的产率得到(R,E)-3-((4S,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolan)]-5-yl)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)prop-2-en-1-ol
  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