(2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-ol | 862670-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-ol
• 英文别名: (2R,3R,5S)-5-[(2R,3R,4R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-4-methyloxan-2-yl]-2-ethenyloxolan-3-ol
• CAS: 862670-45-9
• 化学式: C₁₉H₃₆O₅Si
• 分子量: 372.577
• InChiKey: FKZTWFPBUWCJOT-FEFVAOQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-ol 在 4-二甲氨基吡啶 、 草酰氯 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.33h， 生成 (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-7-oxo-heptanoic acid (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of the common left-half part of pectenotoxins

  摘要：

  The common left-half [C31-C33(OCl-C7)-C40] part of pectenotoxins has been synthesized convergently from the C31-C35, C36-C40, and C1-C7 parts. The C31-C35 part, prepared via a new route shorter than our previous route, was coupled with the C36-C40 part through reductive lithiation and addition reactions to give an adduct stereoselectively, which was converted to a cyclic acetal corresponding to the C31-C40 part. The left-half was synthesized by a three-step process including esterification of the C31-C40 part with the C1-C7 part. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.062
• 作为产物：
  描述：

  (2R,3R)-5-p-methoxybenzyloxy-3-methylpentane-1,2-diol 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 dimethyl pimelimidate dihydrochloride 、 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 碳酸氢钠 、 potassium carbonate 、 二甲基亚砜 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 42.97h， 生成 (2R,3R,5S)-5-[(2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-tetrahydro-pyran-2-yl]-2-vinyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  Synthesis of the common left-half part of pectenotoxins

  摘要：

  The common left-half [C31-C33(OCl-C7)-C40] part of pectenotoxins has been synthesized convergently from the C31-C35, C36-C40, and C1-C7 parts. The C31-C35 part, prepared via a new route shorter than our previous route, was coupled with the C36-C40 part through reductive lithiation and addition reactions to give an adduct stereoselectively, which was converted to a cyclic acetal corresponding to the C31-C40 part. The left-half was synthesized by a three-step process including esterification of the C31-C40 part with the C1-C7 part. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.062

文献信息

• Synthesis of the common left-half part of pectenotoxins
  作者：Kenshu Fujiwara、Masanori Kobayashi、Fuyuki Yamamoto、Yu-ichi Aki、Mariko Kawamura、Daisuke Awakura、Seiji Amano、Azusa Okano、Akio Murai、Hidetoshi Kawai、Takanori Suzuki

  DOI：10.1016/j.tetlet.2005.05.062

  日期：2005.7

  The common left-half [C31-C33(OCl-C7)-C40] part of pectenotoxins has been synthesized convergently from the C31-C35, C36-C40, and C1-C7 parts. The C31-C35 part, prepared via a new route shorter than our previous route, was coupled with the C36-C40 part through reductive lithiation and addition reactions to give an adduct stereoselectively, which was converted to a cyclic acetal corresponding to the C31-C40 part. The left-half was synthesized by a three-step process including esterification of the C31-C40 part with the C1-C7 part. (c) 2005 Elsevier Ltd. All rights reserved.