methyl 4-[(3aR,4R,6aR)-4-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]-4-oxobutanoate | 1451180-04-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 4-[(3aR,4R,6aR)-4-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]-4-oxobutanoate
• CAS: 1451180-04-3
• 化学式: C₁₈H₃₂O₇Si
• 分子量: 388.533
• InChiKey: WAUUCUIIPQOWNF-DWQUBVKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (3aR,5aR,8aR,8bS)-3a-(iodomethyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran 在 dirhodium tetraacetate 、 N-碘代丁二酰亚胺 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.42h， 生成 methyl 4-[(3aR,4R,6aR)-4-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]-4-oxobutanoate
  参考文献：
  名称：

  Ring-Contraction vs Ring-Expansion Reactions of Spiro-cyclopropanecarboxylated Sugars

  摘要：

  Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the Spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.

  DOI：

  10.1021/ol402021e

文献信息

• Ring-Contraction vs Ring-Expansion Reactions of Spiro-cyclopropanecarboxylated Sugars
  作者：Bandi Ramakrishna、Perali Ramu Sridhar

  DOI：10.1021/ol402021e

  日期：2013.9.6

  Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the Spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.