(S)-Acetoxy-[(2R,3S,4R,5S,6S)-6-acetoxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester | 204686-78-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-Acetoxy-[(2R,3S,4R,5S,6S)-6-acetoxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester
• 英文别名: ethyl (2S)-2-acetyloxy-2-[(2R,3S,4R,5S,6S)-6-acetyloxy-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methyloxan-2-yl]acetate
• CAS: 204686-78-2
• 化学式: C₂₆H₅₀O₉Si₂
• 分子量: 562.849
• InChiKey: DGXSYLULYQHDRY-MAGYBIMPSA-N

物化性质

• 沸点：
  522.900±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.047±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-Acetoxy-[(2R,3S,4R,5S,6S)-6-acetoxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 (S)-Acetoxy-((2R,3S,4R,5R,6R)-4,5-diacetoxy-6-allyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Total synthesis of the C37C45 F-ring fragment of spongistatins

  摘要：

  The highly substituted F ring of Spongistatins was synthesized from (R)-(+)-3-benzyloxy-2-methylpropan-1-ol (5), using two sequential Sharpless dihydroxylations as key-steps. A 4-deoxy-4-methyl-D-threo-L-glucoheptopyranose derivative was obtained and could be used to generate the corresponding allyl beta-C-glycoside. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10817-6
• 作为产物：
  描述：

  (S)-[(2R,3S,4R,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-6-oxo-tetrahydro-pyran-2-yl]-hydroxy-acetic acid ethyl ester 在 4-二甲氨基吡啶 、 二异丁基氢化铝 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 (S)-Acetoxy-[(2R,3S,4R,5S,6S)-6-acetoxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  Total synthesis of the C37C45 F-ring fragment of spongistatins

  摘要：

  The highly substituted F ring of Spongistatins was synthesized from (R)-(+)-3-benzyloxy-2-methylpropan-1-ol (5), using two sequential Sharpless dihydroxylations as key-steps. A 4-deoxy-4-methyl-D-threo-L-glucoheptopyranose derivative was obtained and could be used to generate the corresponding allyl beta-C-glycoside. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10817-6