5α-methanesulfonyloxy-4α-hydroxy-2α,10β,20-triacetoxy-11-taxen-13-one | 444307-67-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5α-methanesulfonyloxy-4α-hydroxy-2α,10β,20-triacetoxy-11-taxen-13-one
• CAS: 444307-67-9
• 化学式: C₂₇H₄₀O₁₁S
• 分子量: 572.674
• InChiKey: HJQHXTKJBOGHDQ-CNLUVRCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  159.57
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5α-methanesulfonyloxy-4α-hydroxy-2α,10β,20-triacetoxy-11-taxen-13-one 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 2.5h， 生成 5β,20-epoxy-2α,4α-dihydroxy-10β-acetoxy-11-taxen-13-one
  参考文献：
  名称：

  Synthesis of 7,9-dideoxybaccatin IV analogs from sinenxan A

  摘要：

  Sinenxan A, a taxoid isolated from callus tissue cultures of Taxus yunnanensis was converted into 13-oxo-7,9-dideoxy-2-debenzoyl-2-acetyl-baccatin IV and 7.9-dideoxy-2-debenzoyl-4-deacetyl-baccatin IV, a key framework of 1,7,9-trideoxypaclitaxel. Several special steps in this transformation are worthy of note: (1) deoxygenation by treatment with hypophosphorous acid at C-14 positions (2) a highly regioselective O-deacetylation of taxane:, at C-5 position; and (3) stereoselective reduction of the 13-carbonyl group by transannular assistance from the C-4-hydroxyl. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.03.137
• 作为产物：
  描述：

  2α,5α,10β-triacetoxy-taxa-4(20),11-diene 在 吡啶 、 四氧化锇 、 Celite 、 potassium tert-butylate 、 sodium acetate 、 N-甲基吗啉氧化物 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 25.5h， 生成 5α-methanesulfonyloxy-4α-hydroxy-2α,10β,20-triacetoxy-11-taxen-13-one
  参考文献：
  名称：

  Synthesis of 7,9-dideoxybaccatin IV analogs from sinenxan A

  摘要：

  Sinenxan A, a taxoid isolated from callus tissue cultures of Taxus yunnanensis was converted into 13-oxo-7,9-dideoxy-2-debenzoyl-2-acetyl-baccatin IV and 7.9-dideoxy-2-debenzoyl-4-deacetyl-baccatin IV, a key framework of 1,7,9-trideoxypaclitaxel. Several special steps in this transformation are worthy of note: (1) deoxygenation by treatment with hypophosphorous acid at C-14 positions (2) a highly regioselective O-deacetylation of taxane:, at C-5 position; and (3) stereoselective reduction of the 13-carbonyl group by transannular assistance from the C-4-hydroxyl. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.03.137

文献信息

• Synthetic study of 1,7,9-trideoxypaclitaxel via sinenxan A
  作者：Meng Zhang、Dali Yin、Ji-Yu Guo、Xiao-Tian Liang

  DOI：10.1016/s0040-4039(02)02330-4

  日期：2002.12

  Sinenxan A, a biosynthetic taxane, was converted into compound 9, a key intermediate of 1,7,9-trideoxypaclitaxel. Two special steps in this transformation are worthy of note: (1) regioselective removal of C-5-acetyl; and (2) stereoselective reduction of the 13-carbonyl group by transannular assistance from the C-4-hydroxyl. (C) 2002 Elsevier Science Ltd. All rights reserved.