β-D-lactose octapivalate | 118649-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-lactose octapivalate
• 英文别名: β-lactose octapivalate；beta-Lactose octapivalate；[(2R,3R,4S,5R,6S)-4,5,6-tris(2,2-dimethylpropanoyloxy)-3-[(2S,3R,4S,5S,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 118649-02-8
• 化学式: C₅₂H₈₆O₁₉
• 分子量: 1015.24
• InChiKey: ZDPWELNEAMHDOH-RCGFMNEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  71
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  β-D-lactose octapivalate 生成 pivaloyl(-2)[pivaloyl(-3)][pivaloyl(-4)][pivaloyl(-6)]Gal(b1-4)[pivaloyl(-2)][pivaloyl(-3)][pivaloyl(-6)]Glc
  参考文献：
  名称：

  ZIMMERMANN, PETER;BOMMER, RENE;BAR, THOMAS;SCHMIDT, RICHARD R., J. CARBOHYDR. CHEM., 7,(1988) N 12, 435-452

  摘要：

  DOI：
• 作为产物：
  描述：

  lactose 生成 β-D-lactose octapivalate
  参考文献：
  名称：

  ZIMMERMANN, PETER;BOMMER, RENE;BAR, THOMAS;SCHMIDT, RICHARD R., J. CARBOHYDR. CHEM., 7,(1988) N 12, 435-452

  摘要：

  DOI：

文献信息

• Efficient Stereoselective Glycosylations of Alcohols by Sugar Perpivalates: The First Use of 1-O-Pivaloylated Glycosyl Donors
  作者：Han Zuilhof、Aliaksei Pukin

  DOI：10.1055/s-0029-1218361

  日期：2009.12

  1-O-Pivaloyl glycosides were shown to be efficient glycosyl donors by using the perpivaloylated derivatives of lactose, galactose and glucose in the direct ZnCl2-promoted glycosylations of various alcohols. The corresponding glycosides were isolated in good yields and β-selectivity.

  在 ZnCl2 直接促进的各种醇的糖基化反应中，通过使用乳糖、半乳糖和葡萄糖的过新戊酰化衍生物，证明 1-O-Pivaloyl 糖苷是高效的糖基供体。分离出的相应糖苷具有良好的产率和δ选择性。
• SnCl4: An efficient and inexpensive promoter for synthesis of ω-functionalized alkyl 1,2-trans-glycosides from 1-O-pivaloyl donor
  作者：A. Nikseresht

  DOI：10.1134/s1070363216010266

  日期：2016.1

  SnCl4-promoted reactions of perpivaloylated lactose with various alcohols were studied in the presence or absence of an additive, CaCO3. SnCl4 was found to promote the 1,2-trans-glycosylation of alcohols in CH2Cl2 at 0A degrees C in a stereo controlled manner with beta-selectivity. The corresponding glycosides were isolated in high yields.
• ZIMMERMANN, PETER;BOMMER, RENE;BAR, THOMAS;SCHMIDT, RICHARD R., J. CARBOHYDR. CHEM., 7,(1988) N 12, 435-452
  作者：ZIMMERMANN, PETER、BOMMER, RENE、BAR, THOMAS、SCHMIDT, RICHARD R.

  DOI：——

  日期：——