4α,5α-dihydroxy-2α,10β,13α,20-tetraacetoxy-11-taxene | 496041-99-7

• 英文名称: 4α,5α-dihydroxy-2α,10β,13α,20-tetraacetoxy-11-taxene
• 英文别名: [(1R,2R,3R,4S,5S,8S,10S,13S)-2,10,13-triacetyloxy-4,5-dihydroxy-8,12,15,15-tetramethyl-4-tricyclo[9.3.1.03,8]pentadec-11-enyl]methyl acetate
• CAS: 496041-99-7
• 化学式: C₂₈H₄₂O₁₀
• 分子量: 538.635
• InChiKey: CEXIPTGSALYLGX-LGTYCVOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4α,5α-dihydroxy-2α,10β,13α,20-tetraacetoxy-11-taxene 在 吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 60.5h， 生成 5α-methanesulfonyloxy-2α,4α,20-trihydroxy-10β,13α-diacetoxy-11-taxene
  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-4(20),11-taxadien-13-one 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 potassium tert-butylate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 21.0h， 生成 4α,5α-dihydroxy-2α,10β,13α,20-tetraacetoxy-11-taxene
  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.