(1R,2S,3R,4S)-3-endo-Chloro-5-oxo-2-endo-(phenylseleno)-7-oxabicyclo<2.2.1>hept-2-exo-yl 3'-chlorobenzoate | 170873-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S,3R,4S)-3-endo-Chloro-5-oxo-2-endo-(phenylseleno)-7-oxabicyclo<2.2.1>hept-2-exo-yl 3'-chlorobenzoate
• 英文别名: [(1R,2S,3R,4S)-3-chloro-5-oxo-2-phenylselanyl-7-oxabicyclo[2.2.1]heptan-2-yl] 3-chlorobenzoate
• CAS: 170873-07-1
• 化学式: C₁₉H₁₄Cl₂O₄Se
• 分子量: 456.184
• InChiKey: YOFMWRQMPCPNAM-NTDBWNAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S)-3-endo-Chloro-5-oxo-2-endo-(phenylseleno)-7-oxabicyclo<2.2.1>hept-2-exo-yl 3'-chlorobenzoate 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 1.17h， 生成 (1S,4R,5S,6S)-6-Chloro-5-hydroxy-7-oxa-bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Synthesis of Undeculofuranoside Derivatives of the Herbicidins and of Analogs

  摘要：

  The condensation of 3-O-(tert-butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-alpha-D-xylo-hexodialdo-1,4-furanose (obtained in six steps (35%) from D-glucurono-6,3-lactone) with the lithium enolate of (+/-)6-endo-chloro-5-endo-(methoxymethoxy)-7-oxabicyclo[2.2.1]heptan-2-one (derived in six steps (25%) from the Diels-Alder adduct of furan to 1-cyanovinyl acetate) was highly exo face selective giving two major aldols that were separated readily. One of them was converted to 6,10-anhydro-5-deoxy-1,2-O-isopropylidene-9-O-(methoymethyl)-alpha-D-arabino-L-ido-7-undeculofuranose-(1,4)-pyranose-(7,3), a semiprotected form of the long-chain carbohydrate moiety of the herbicidins. The synthesis implies the acid-promoted isomerization of 10,11-anhydro-5,7-dideoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-[(2-nitrophenyl)selenomethyl]-beta-L-ido-L-ido-undecofuranose.

  DOI：

  10.1021/jo00123a021
• 作为产物：
  描述：

  (-)-(1S,4R,5R,6R)-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one 在 sodium acetate 、 乙酸酐 、 间氯过氧苯甲酸 作用下， 生成 (1RS,4RS)-6-Chloro-5-(phenylseleno)-7-oxabicyclo<2.2.1>hept-5-en-2-one 、 (1R,2S,3R,4S)-3-endo-Chloro-5-oxo-2-endo-(phenylseleno)-7-oxabicyclo<2.2.1>hept-2-exo-yl acetate 、 (1R,2S,3R,4S)-3-endo-Chloro-5-oxo-2-endo-(phenylseleno)-7-oxabicyclo<2.2.1>hept-2-exo-yl 3'-chlorobenzoate
  参考文献：
  名称：

  Synthesis of Undeculofuranoside Derivatives of the Herbicidins and of Analogs

  摘要：

  The condensation of 3-O-(tert-butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-alpha-D-xylo-hexodialdo-1,4-furanose (obtained in six steps (35%) from D-glucurono-6,3-lactone) with the lithium enolate of (+/-)6-endo-chloro-5-endo-(methoxymethoxy)-7-oxabicyclo[2.2.1]heptan-2-one (derived in six steps (25%) from the Diels-Alder adduct of furan to 1-cyanovinyl acetate) was highly exo face selective giving two major aldols that were separated readily. One of them was converted to 6,10-anhydro-5-deoxy-1,2-O-isopropylidene-9-O-(methoymethyl)-alpha-D-arabino-L-ido-7-undeculofuranose-(1,4)-pyranose-(7,3), a semiprotected form of the long-chain carbohydrate moiety of the herbicidins. The synthesis implies the acid-promoted isomerization of 10,11-anhydro-5,7-dideoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-[(2-nitrophenyl)selenomethyl]-beta-L-ido-L-ido-undecofuranose.

  DOI：

  10.1021/jo00123a021

文献信息

• Synthesis of Undeculofuranoside Derivatives of the Herbicidins and of Analogs
  作者：Fabienne Emery、Pierre Vogel

  DOI：10.1021/jo00123a021

  日期：1995.9

  The condensation of 3-O-(tert-butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-alpha-D-xylo-hexodialdo-1,4-furanose (obtained in six steps (35%) from D-glucurono-6,3-lactone) with the lithium enolate of (+/-)6-endo-chloro-5-endo-(methoxymethoxy)-7-oxabicyclo[2.2.1]heptan-2-one (derived in six steps (25%) from the Diels-Alder adduct of furan to 1-cyanovinyl acetate) was highly exo face selective giving two major aldols that were separated readily. One of them was converted to 6,10-anhydro-5-deoxy-1,2-O-isopropylidene-9-O-(methoymethyl)-alpha-D-arabino-L-ido-7-undeculofuranose-(1,4)-pyranose-(7,3), a semiprotected form of the long-chain carbohydrate moiety of the herbicidins. The synthesis implies the acid-promoted isomerization of 10,11-anhydro-5,7-dideoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-[(2-nitrophenyl)selenomethyl]-beta-L-ido-L-ido-undecofuranose.