(4S)-4-[[(4aS,6R,8S,8aR)-4-amino-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-6-yl]methyl]-1,3-dioxolan-2-one | 195703-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (4S)-4-[[(4aS,6R,8S,8aR)-4-amino-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-6-yl]methyl]-1,3-dioxolan-2-one
• CAS: 195703-12-9
• 化学式: C₁₄H₂₃NO₇
• 分子量: 317.339
• InChiKey: LYBCMOKTSNUSMR-ZFOIQSNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S)-4-[[(4aS,6R,8S,8aR)-4-amino-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-6-yl]methyl]-1,3-dioxolan-2-one 在 potassium tert-butylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 山海绵酰胺A
  参考文献：
  名称：

  Total synthesis of mycalamides A and B

  摘要：

  DOI：

  10.1021/jo00301a007
• 作为产物：
  描述：

  (4S)-4-[[(4aS,6R,8S,8aR)-4-azido-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-6-yl]methyl]-1,3-dioxolan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (4S)-4-[[(4aS,6R,8S,8aR)-4-amino-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-6-yl]methyl]-1,3-dioxolan-2-one
  参考文献：
  名称：

  Total synthesis of mycalamides A and B

  摘要：

  DOI：

  10.1021/jo00301a007

文献信息

• Total synthesis of mycalamides A and B
  作者：Chang Yong Hong、Yoshito Kishi

  DOI：10.1021/jo00301a007

  日期：1990.7
• Synthesis and biological activity of artificial analogs of mycalamide A
  作者：Hideto Fukui、Yoshinori Tsuchiya、Keiko Fujita、Tadakiyo Nakagawa、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1016/s0960-894x(97)00365-x

  日期：1997.8

  Artificial analogs of mycalamide A, a potent antitumor and antiviral compound isolated from a New Zealand marine sponge, were synthesized and their biological activities were tested. (C) 1997 Published by Elsevier Science Ltd.
• HONG, CHANG YONG;KISHI, YOSHITO, J. ORG. CHEM., 55,(1990) N4, C. 4242-4245
  作者：HONG, CHANG YONG、KISHI, YOSHITO

  DOI：——

  日期：——
• Total Synthesis of Mycalamide A. Further Synthetic Study of the Right Half
  作者：Tadashi Nakata、Hideto Fukui、Tadakiyo Nakagawa、Hiroko Matsukura

  DOI：10.3987/com-95-s64

  日期：——

  The right half 5 of mycalamide A (1) was synthesized starting from (R)- or (S)-pantolactone via the Sharpless asymmetric dihydroxylation as the key step. The total synthesis of mycalamide A (1) was accomplished by coupling of the right and left halves.