(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 | 204686-85-1

• 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: (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
• 英文别名: ethyl (2S)-2-[(2R,3S,4R,5S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methyl-6-oxooxan-2-yl]-2-hydroxyacetate
• CAS: 204686-85-1
• 化学式: C₂₂H₄₄O₇Si₂
• 分子量: 476.758
• InChiKey: FUSUEZQYVTYJDD-AVEIZBFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  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 、 三氟甲磺酸三甲基硅酯 、 二异丁基氢化铝 作用下， 以 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.5h， 生成 (S)-Acetoxy-((2R,3S,4R,5S,6S)-4,5,6-triacetoxy-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：

  (2S,3R,4S,5R,6S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-4-methyl-heptanedioic acid diethyl ester 在 2,6-二甲基吡啶 、 氢氟酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.0h， 生成 (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
  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