methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-D-glycero-D-galacto-octanoate | 158014-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-D-glycero-D-galacto-octanoate
• CAS: 158014-11-0
• 化学式: C₁₂H₂₀O₇
• 分子量: 276.287
• InChiKey: OXRZMYZOWAVWKD-HYDRHDSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  94.45
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-D-glycero-D-galacto-octanoate 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 生成 ((3aR,4S,6S,6aR)-6-Formyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Enantiospecific syntheses of (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone

  摘要：

  D-Mannose has been converted by six sequential reactions (acetonation, Wittig-intramolecular Michael reaction, selective deacetonation, glycol cleavage oxidation and Grignard reaction) into the methyl esters 9 and 10 which underwent a de-isopropylidenation reaction with concommitant lactonisation to give the (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone 1 and 2.

  DOI：

  10.1016/0957-4166(94)80168-1
• 作为产物：
  描述：

  2,3,5,6-di-O-isopropylidene-D-mannofuranose 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 112.0h， 生成 methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-D-glycero-D-galacto-octanoate
  参考文献：
  名称：

  Enantiospecific syntheses of (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone

  摘要：

  D-Mannose has been converted by six sequential reactions (acetonation, Wittig-intramolecular Michael reaction, selective deacetonation, glycol cleavage oxidation and Grignard reaction) into the methyl esters 9 and 10 which underwent a de-isopropylidenation reaction with concommitant lactonisation to give the (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone 1 and 2.

  DOI：

  10.1016/0957-4166(94)80168-1

文献信息

• Enantiospecific syntheses of (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone
  作者：Tony K.M. Shing、Hon-Chung Tsui

  DOI：10.1016/0957-4166(94)80168-1

  日期：1994.7

  D-Mannose has been converted by six sequential reactions (acetonation, Wittig-intramolecular Michael reaction, selective deacetonation, glycol cleavage oxidation and Grignard reaction) into the methyl esters 9 and 10 which underwent a de-isopropylidenation reaction with concommitant lactonisation to give the (3S,4R)- and (3S,4R,7S)-diastereoisomers of goniofufurone 1 and 2.