[(3aR,4R,6R,7R,7aR)-7-acetyloxy-2,2-dimethyl-4-(2-phenylethynyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]methyl acetate | 1013036-26-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(3aR,4R,6R,7R,7aR)-7-acetyloxy-2,2-dimethyl-4-(2-phenylethynyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]methyl acetate
• CAS: 1013036-26-4
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: XYVDEJVZSLGSED-WAPOTWQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  1,4,6-三-O-乙酰基-2,3-O-亚异丙基-A-D-吡喃甘露糖 、 (碘乙炔基)苯 在 indium 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以66%的产率得到[(3aR,4R,6R,7R,7aR)-7-acetyloxy-2,2-dimethyl-4-(2-phenylethynyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]methyl acetate
  参考文献：
  名称：

  Direct C-Glycosylation by Indium-Mediated Alkynylation on Sugar Anomeric Position

  摘要：

  Indium-mediated alkynylation reaction was studied for the direct preparation of C-glycosides. Easily available starting sugar derivatives with an acetyl group at the anomeric position were tested as electrophiles toward alkynylindium reagents under Barbier conditions. Good yields and stereoselectivities were observed during the reaction. The alkynylation was applied to the synthesis of an alpha-(1 -> 6)-C-disaccharide analogue of isomaltoside.

  DOI：

  10.1021/ol7029257

文献信息

• PROCESS FOR PREPARING MANNOSE DERIVATIVES
  申请人：ENTEROME

  公开号：US20210309682A1

  公开（公告）日：2021-10-07

  The invention relates to a process to prepare a compound of the following formula (I): (I), in which P represents a protective group of a hydroxyl function which is a —COR 1 group with R 1 representing an aryl or a (C 1 C 6 )alkyl, R represents a hydrogen atom or a protective group of a terminal alkyne, from mannose, comprising the following steps: (a) protecting the 5 hydroxyl groups of the mannose by a protective group P; (b) coupling the protected mannose obtained at step (a) with a compound of the following formula (II). The present invention also relates to a compound of formula (IIIa).