(3aR,3bS,6aR,7aR)-tetrahydro-2,2,5,5-tetramethyl-6aH-cyclopenta[1,2-d:3,4-d']bis[1,3]dioxole-6a-carboxaldehyde | 288589-54-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,3bS,6aR,7aR)-tetrahydro-2,2,5,5-tetramethyl-6aH-cyclopenta[1,2-d:3,4-d']bis[1,3]dioxole-6a-carboxaldehyde
• 英文别名: (1R,2S,6R,8R)-4,4,10,10-tetramethyl-3,5,9,11-tetraoxatricyclo[6.3.0.02,6]undecane-6-carbaldehyde
• CAS: 288589-54-8
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: PGGVFBFDIFCTGO-XBWDGYHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,3bS,6aR,7aR)-tetrahydro-2,2,5,5-tetramethyl-6aH-cyclopenta[1,2-d:3,4-d']bis[1,3]dioxole-6a-carboxaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以85%的产率得到(3aR,3bS,6aR,7aR)-tetrahydro-2,2,5,5-tetramethyl-6aH-cyclopenta[1,2-d:3,4-d']bis[1,3]dioxole-6a-methanol
  参考文献：
  名称：

  Intramolecular alkylation of ε-iodo, α-alkoxy aldehydes

  摘要：

  The base-mediated intramolecular alkylation of 6-deoxy-6-iodo-2,3:4,5-di-O-isopropylide-D-glucose (2) leading to the polyfunctionalized cyclopentane 4 is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00838-8
• 作为产物：
  描述：

  6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-D-glucose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到(3aR,3bS,6aR,7aR)-tetrahydro-2,2,5,5-tetramethyl-6aH-cyclopenta[1,2-d:3,4-d']bis[1,3]dioxole-6a-carboxaldehyde
  参考文献：
  名称：

  Intramolecular alkylation of ε-iodo, α-alkoxy aldehydes

  摘要：

  The base-mediated intramolecular alkylation of 6-deoxy-6-iodo-2,3:4,5-di-O-isopropylide-D-glucose (2) leading to the polyfunctionalized cyclopentane 4 is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00838-8

文献信息

• Synthesis of higher-carbon sugars by addition of organometallic reagents to aldehydes or lactols derived from carbohydrates
  作者：José Marco-Contelles、Elsa de Opazo、Nieves Arroyo

  DOI：10.1016/s0040-4020(01)00410-0

  日期：2001.5

  The addition of different Grignard or lithium organometallic reagents to lactols (1, 6, 21) or aldehydes (10), derived from d-glucose or d-mannose, to give the new higher-carbon sugars (2, 3, 7–9, 13–19, 22 and 23) is reported.

  加入不同格氏试剂或锂有机金属试剂的至内半缩醛（1，6，21）或醛（10）中，从d-葡萄糖或d甘露糖衍生的，以得到新的更高碳糖（2，3，7 - 9，13 - 19，22和23）进行报告。
• Intramolecular alkylation of ε-iodo, α-alkoxy aldehydes
  作者：José Marco-Contelles、Elsa de Opazo

  DOI：10.1016/s0040-4039(00)00838-8

  日期：2000.7

  The base-mediated intramolecular alkylation of 6-deoxy-6-iodo-2,3:4,5-di-O-isopropylide-D-glucose (2) leading to the polyfunctionalized cyclopentane 4 is described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• SOME UNEXPECTED RESULTS IN DONDONI'S ONE-CARBON HOMOLOGATION PROCEDURE1
  作者：José Marco-Contelles、Elsa de Opazo

  DOI：10.1081/car-100108278

  日期：——

  The formation of the unexpected secondary products (3 and 9) during Dondoni's one-carbon homologation of 6-deoxy-6-iodo-2,3:4,5-bis-Ow-isopropylidene-D-glucose (1) are described.