10,11-Anhydro-3-O-(tert-butyldimethylsilyl)-5,7-dideoxy-1,2:8,9-di-O-isopropylidene-7-C-methylidene-β-L-xylo-L-ido-undecofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10,11-Anhydro-3-O-(tert-butyldimethylsilyl)-5,7-dideoxy-1,2:8,9-di-O-isopropylidene-7-C-methylidene-β-L-xylo-L-ido-undecofuranose
• 英文别名: (2R)-1-[(3aR,5R,6S,6aR)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-[(4R,5S)-2,2-dimethyl-5-[(2S)-oxiran-2-yl]-1,3-dioxolan-4-yl]but-3-en-2-ol
• 化学式: C₂₄H₄₂O₈Si
• 分子量: 486.678
• InChiKey: RCEYQAIQMKLOPX-BRNKUGCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-1,2:8,9-di-O-isopropylidene-7-C-methylidene-α-D-arabino-L-ido-undecofuranose 在 N,N-二甲基丙烯基脲 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以56%的产率得到10,11-Anhydro-3-O-(tert-butyldimethylsilyl)-5,7-dideoxy-1,2:8,9-di-O-isopropylidene-7-C-methylidene-β-L-xylo-L-ido-undecofuranose
  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.