(3S,4R,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-methyl-tetrahydro-pyran-2-one | 212767-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4R,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-methyl-tetrahydro-pyran-2-one
• 英文别名: (3S,4R,5R,6R)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-5-methyloxan-2-one
• CAS: 212767-69-6
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: VXTHCDMOAQHLBA-GOFVFXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-methyl-tetrahydro-pyran-2-one 在 咪唑 、 三氟乙酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,4S,4aR,9aS)-3-((R)-1,2-Dihydroxy-ethyl)-6,6,8,8-tetraisopropyl-4-methyl-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocyclohepten-1-one
  参考文献：
  名称：

  Synthesis and biological activity of lactones en route to Altohyrtin A

  摘要：

  Lactones 2 and 7 were synthesised and tested against six human tumour cell lines (Pancrens-a, BXPC-3), (Thyroid ca, KAT-4), (Thyroid ca, SW1736), (Lung-NSC, NCI-H460), (Pharynx-sq, FADU) and (Prostate, DU-145). Lactone 7 proved inactive, but lactone 2 displayed some activity against four of the six cell lines examined. Both lactones were converted into an intermediate 5 en route to Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00268-6
• 作为产物：
  描述：

  (2S,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-4-methyl-pentanoic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (3S,4R,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-methyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Synthesis and biological activity of lactones en route to Altohyrtin A

  摘要：

  Lactones 2 and 7 were synthesised and tested against six human tumour cell lines (Pancrens-a, BXPC-3), (Thyroid ca, KAT-4), (Thyroid ca, SW1736), (Lung-NSC, NCI-H460), (Pharynx-sq, FADU) and (Prostate, DU-145). Lactone 7 proved inactive, but lactone 2 displayed some activity against four of the six cell lines examined. Both lactones were converted into an intermediate 5 en route to Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00268-6

文献信息

• Synthesis and biological activity of lactones en route to Altohyrtin A
  作者：Stephen A. Hermitage、Alison Murphy、Stanley M. Roberts

  DOI：10.1016/s0960-894x(98)00268-6

  日期：1998.7

  Lactones 2 and 7 were synthesised and tested against six human tumour cell lines (Pancrens-a, BXPC-3), (Thyroid ca, KAT-4), (Thyroid ca, SW1736), (Lung-NSC, NCI-H460), (Pharynx-sq, FADU) and (Prostate, DU-145). Lactone 7 proved inactive, but lactone 2 displayed some activity against four of the six cell lines examined. Both lactones were converted into an intermediate 5 en route to Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.