1,2:3,4-di-O-isopropylidene-6-O-(allenyl)-α-D-galactopyranoside | 149156-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1,2:3,4-di-O-isopropylidene-6-O-(allenyl)-α-D-galactopyranoside
• 英文别名: (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-5-((propa-1,2-dien-1-yloxy)methyl)tetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran
• CAS: 149156-98-9
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: ZXADBDNWCNYZMB-KSSYENDESA-N

物化性质

• 沸点：
  365.9±37.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2:3,4-di-O-isopropylidene-6-O-(allenyl)-α-D-galactopyranoside 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 丙酮 为溶剂， 反应 17.0h， 以89%的产率得到双丙酮半乳糖
  参考文献：
  名称：

  Study of metal and acid catalysed deprotection of propargyl ethers of alcohols via their allenyl ethers

  摘要：

  A new method for the deprotection of prop-2-ynyl ethers 1b-9b is described. Isomerisation of 1b-9b to O-allenyl ethers 1d-9d and deprotection by reaction with Hg(OCOCF3)(2), aq.HCl, aq.CF3CO2H and best by use of a catalytic amount of OsO4 is described to obtain the alcohols 1a-9a in good yield. Application of this method for the deprotection of prop-2-enyl ethers 7c,8c,10c-13c via their corresponding prop-1-enyl ethers 7e,8e,10e-13e to obtain the corresponding alcohols 7a,8a,10a-13a is also described, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00631-6
• 作为产物：
  描述：

  1,2:3,4-di-O-isopropylidene-6-O-(prop-2-ynyl)-α-D-galactopyranoside 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 以83%的产率得到1,2:3,4-di-O-isopropylidene-6-O-(allenyl)-α-D-galactopyranoside
  参考文献：
  名称：

  An Efficient Synthesis of Enantiopure 1-Alkoxy-1,2-propadienes from Propargyl Bromide

  摘要：

  一系列对映纯功能化醇通过其相应钠醇盐与丙炔溴化物反应后，再经过t-BuOK催化的异构化反应，对得到的丙炔醚进行O-烯丙基化，获得了良好的总体产率。

  DOI：

  10.1055/s-1994-25577

文献信息

• Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol
  作者：Hao Guo、Jan‐Lukas Kirchhoff、Carsten Strohmann、Bastian Grabe、Charles C. J. Loh

  DOI：10.1002/anie.202400912

  日期：2024.5.21

  Herein, we demonstrate the robustness of a synergistic chiral Pd/organoboron system in tackling a challenging suite of site‐, regio‐, enantio‐ and diastereoselectivity issues across a considerable palette of biologically relevant carbohydrate polyols, when prochiral alkoxyallenes were employed as electrophiles. In view of the burgeoning role of noncovalent interactions (NCIs) in stereoselective carbohydrate synthesis, our mechanistic experiments and DFT modeling of the reaction path unexpectedly revealed that NCIs such as hydrogen bonding and CH‐π interactions between the resting states of the Pd‐π‐allyl complex and the borinate saccharide are critically involved in the stereoselectivity control. Our strategy thus illuminates the untapped potential of harnessing NCIs in the context of transition metal catalysis to tackle stereoselectivity challenges in carbohydrate functionalization.