3,5-O-Isopropylidene-D-glycero-D-gulo-heptono-γ-lactone | 6605-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-O-Isopropylidene-D-glycero-D-gulo-heptono-γ-lactone
• 英文别名: 3,5-O-Isopropyliden-D-glycero-D-gulo-heptono-γ-lacton；(4R,4aS,7R,7aS)-4-[(1R)-1,2-dihydroxyethyl]-7-hydroxy-2,2-dimethyl-4,4a,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-6-one
• CAS: 6605-23-8
• 化学式: C₁₀H₁₆O₇
• 分子量: 248.233
• InChiKey: VNWZDEHQBWMJEY-YQXRAVKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-O-Isopropylidene-D-glycero-D-gulo-heptono-γ-lactone 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以100%的产率得到
  参考文献：
  名称：

  Total synthesis of antitumour agent (+)-goniofufurone

  摘要：

  通过D-甘油-D-古洛-庚酮-γ-内酯的短程立体选择性合成，分八步合成，天然的角尼呋喃酮的绝对构型为1，总产率为12.7%。

  DOI：

  10.1039/c39920000810
• 作为产物：
  描述：

  葡庚糖酸内酯 在 磷酸 、 溶剂黄146 、 zinc(II) chloride 作用下， 反应 48.0h， 生成 3,5-O-Isopropylidene-D-glycero-D-gulo-heptono-γ-lactone
  参考文献：
  名称：

  Total synthesis of antitumour agent (+)-goniofufurone

  摘要：

  通过D-甘油-D-古洛-庚酮-γ-内酯的短程立体选择性合成，分八步合成，天然的角尼呋喃酮的绝对构型为1，总产率为12.7%。

  DOI：

  10.1039/c39920000810

文献信息

• Total synthesis of antitumour agent (+)-goniofufurone
  作者：Tony K. M. Shing、Hon-Chung Tsui、Zhao-Hui Zhou

  DOI：10.1039/c39920000810

  日期：——

  The absolute configuration of the natural goniofufurone is confirmed as 1 by a short and stereoselective synthesis in eight steps from D-glycero-D-gulo-heptono-γ-lactone with an overall yield of 12.7%.

  通过D-甘油-D-古洛-庚酮-γ-内酯的短程立体选择性合成，分八步合成，天然的角尼呋喃酮的绝对构型为1，总产率为12.7%。
• Enantiospecific Syntheses of (+)-Goniofufurone, (+)-7-epi-Goniofufurone, (+)-Goniobutenolide A, (-)-Goniobutenolide B, (+)-Goniopypyrone, (+)-Altholactone, (+)-Goniotriol, and (+)-7-Acetylgoniotriol
  作者：Tony K. M. Shing、Hon-Chung Tsui、Zhao-Hui Zhou

  DOI：10.1021/jo00115a030

  日期：1995.5

  Practical and efficient syntheses of a number of styryl lactones with various structural complexities were accomplished from commercially available and inexpensive D-glycero -D-gulo-heptono-gamma-lactone (D-glucoheptonic gamma-lactone)(11). Lactone 11 was converted by four sequential reactions (acetonation, selective deacetonation, glycol cleavage oxidation, and Grignard reaction) into key intermediates 3,5-O-isopropylidene-1, 1,6-tri-C-phenyl-D-glycero-D-gulo-hexitol (15) and 3,5-O-isopropylidene-1,1,6-tri-C-phenyl-L-glycero-D-gulo- hexitol(16). The alcohol 15 was transformed via a glycol cleavage oxidation and a Z-selective Wittig reaction into enoate Z-9 which underwent hydrolysis and an intramolecular Michael-type cyclization to give (+)-goniofufurone (1). Likewise, reaction of 16 afforded 7-epi-goniofufurone (2). Acylation and subsequent deacylation of 7-C-phenyl-D-gluco-hept-2-enono-gamma-lactone (20) readily gave (+)-goniobutenolide A (3) and (-)-goniobutenolide B (4), whereas treatment of (Z)-methyl 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enonate (Z-22) with DBU followed by acid hydrolysis and intramolecular Michael reaction provided (+)-goniopypyrone (5). Mesylation of 4,6-O-isopropylidene-7-C-phenyl-L-ido-hept-2-enono-delta- lactone (27) followed by acid hydrolysis furnished (+)-altholactone (6). (+)-Goniotriol (7) and (+)-7-acetylgoniotriol (8) were readily obtained from the enoate Z-9. This work also provides a viable synthetic route for the construction of the enantiomers of the above styryl lactones for biological evaluation from the same starting material 11. Suggestions about the possible biosynthetic pathway of the styryl lactones are given.