(1aS,3R,3aS,6aS,6bR)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-tetrahydro-1,2,4,6-tetraoxa-cyclopropa[e]inden-5-one | 220811-68-7

• 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: (1aS,3R,3aS,6aS,6bR)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-tetrahydro-1,2,4,6-tetraoxa-cyclopropa[e]inden-5-one
• CAS: 220811-68-7
• 化学式: C₁₃H₂₂O₆Si
• 分子量: 302.4
• InChiKey: DPTNDGYKLXVRBV-ZKKRXERASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  66.52
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1aS,3R,3aS,6aS,6bR)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-tetrahydro-1,2,4,6-tetraoxa-cyclopropa[e]inden-5-one 在 吡啶 、 2,6-二叔丁基吡啶 、 4 A molecular sieve 、 silver perchlorate 、 tin(ll) chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 [(2S,3R,4R,5S,6S)-6-[[(3aS,4R,6R,7R,7aS)-6-[[(2R,3S,4R)-3-acetyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-4-yl]oxy]-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-oxo-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-2-methyl-4,5-bis(phenylmethoxy)oxan-3-yl] benzoate
  参考文献：
  名称：

  Application of the Glycal Assembly Method to the Concise Synthesis of Neoglycoconjugates of Ley and Leb Blood Group Determinants and of H-Type I and H-Type II Oligosaccharides

  摘要：

  The power of the glycal assembly strategy for reaching Lewis and H-type blood group determinants is demonstrated herein. Three key elements form the basis of the method. Thus, alpha-epoxides derived from galactal cyclic carbonate 13 are produced stereospecifically and are highly effective beta-galactosyl donors. Also, 6-monoprotected glucals can be regiospecifically glycosylated at the C-3 hydroxyl (see 23 + 13 --> 24). Moreover, glycosylation via a glycal epoxide produces a unique C-2 hydroxyl in the product which can be exploited as the acceptor site for branching (see formation of 26).

  DOI：

  10.1021/ja00126a011
• 作为产物：
  描述：

  (2R,3R,4R)-2-(羟基甲基)-3,4-二氢-2H-吡喃-3,4-二醇 在 咪唑 、 二甲基二环氧乙烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.0h， 生成 (1aS,3R,3aS,6aS,6bR)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-tetrahydro-1,2,4,6-tetraoxa-cyclopropa[e]inden-5-one
  参考文献：
  名称：

  Application of Glycals to the Synthesis of Oligosaccharides: Convergent Total Syntheses of the Lewis X Trisaccharide Sialyl Lewis X Antigenic Determinant and Higher Congeners

  摘要：

  Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLe(x) tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation-rearrangement step allows for the use of minimally protected glycosides as the glycosyl accepters. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Le(x) glycal.

  DOI：

  10.1021/ja00112a007

文献信息

• Gold(I)-Catalyzed Glycosidation of 1,2-Anhydrosugars
  作者：Yao Li、Pingping Tang、Youxi Chen、Biao Yu

  DOI：10.1021/jo8003875

  日期：2008.6.1

  Being able to increase the yield by >20% compared to the conventional use of anhydrous zinc chloride (>1 equiv) as a promoter, Ph3PAuOTf is disclosed to be a superior catalyst for the well-established glycosylation reaction with 1,2-anhydrosugars as donors.