((3aR,4S,6S,6aR)-6-Formyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester | 158014-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aR,4S,6S,6aR)-6-Formyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester
• 英文别名: methyl 2-[(3aR,4S,6S,6aR)-4-formyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]acetate
• CAS: 158014-12-1
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: OYVLRAKEEQZOFR-WDQPUEAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((3aR,4S,6S,6aR)-6-Formyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 3,6-anhydro-2-deoxy-7-C-phenyl-D-glycero-D-galacto-heptono-1,4-lactone
  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 periodate 、 溶剂黄146 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 64.25h， 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

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.