[(3aR,4R,7aR)-6-heptadecyl-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy-tert-butyl-diphenylsilane | 224324-95-2

• 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: [(3aR,4R,7aR)-6-heptadecyl-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 224324-95-2
• 化学式: C₄₂H₆₆O₄Si
• 分子量: 663.069
• InChiKey: AOROLRFBPMMBFS-ACUYYCNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.63
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,7aR)-6-heptadecyl-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy-tert-butyl-diphenylsilane 在 dimethyl sulfide borane 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 以76%的产率得到(1S)-1,5-anhydro-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-D-galactitol
  参考文献：
  名称：

  C-Glycoside analogues of β-galactosylceramide with a simple ceramide substitute: Synthesis and binding to HIV-1 gp120

  摘要：

  The synthesis and HIV-1 gp120 binding of C- and aza-C-glycoside analogues of beta-galactosylceramide (GalCer) that contain a simple C-17 hydrocarbon chain as a ceramide substitute are described. Both compounds originate from stearic acid, and a carbohydrate-derived thioacetal-alcohol, and their syntheses are potentially general for beta-C-galactosides and their aza-C-partners. They showed potent and specific affinity for gp120 in an assay based on the change of surface pressure when the glycolipid monolayers were exposed to Solutions of gp120. Interestingly, the aza-C-glycoside exhibited a significantly higher affinity than GalCer, whereas the C-glycoside was as active as GalCer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.044
• 作为产物：
  描述：

  (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol 在 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 三氟化硼乙醚 、 碘 、 sodium methylate 、 N,N'-二环己基碳二亚胺 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 [(3aR,4R,7aR)-6-heptadecyl-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy-tert-butyl-diphenylsilane
  参考文献：
  名称：

  1-Thio-1,2-O-isopropylidene Acetals:  Novel Precursors for the Synthesis of Complex C-Glycosides

  摘要：

  DOI：

  10.1021/ja9843270

文献信息

• Synthesis of aza-C-galacto disaccharides from C1-substituted galactals
  作者：Xuhong Cheng、Govindaraj Kumaran、David R. Mootoo

  DOI：10.1039/b101598m

  日期：——

  C1-substituted galactals are transformed via the double reductive amination on their 1,5-diketone derivatives, to aza-β-C-galacto-disaccharides.

  C1-取代半乳糖醛通过其1,5-二酮衍生物上的双还原胺化反应转化为氮杂-β-C-半乳糖二糖。
• 1-Thio-1,2-<i>O</i>-isopropylidene Acetals:  Novel Precursors for the Synthesis of Complex <i>C</i>-Glycosides
  作者：Noshena Khan、Xuhong Cheng、David R. Mootoo

  DOI：10.1021/ja9843270

  日期：1999.5.1
• C-Glycoside analogues of β-galactosylceramide with a simple ceramide substitute: Synthesis and binding to HIV-1 gp120
  作者：Line A. Augustin、Jacques Fantini、David R. Mootoo

  DOI：10.1016/j.bmc.2005.09.044

  日期：2006.2

  The synthesis and HIV-1 gp120 binding of C- and aza-C-glycoside analogues of beta-galactosylceramide (GalCer) that contain a simple C-17 hydrocarbon chain as a ceramide substitute are described. Both compounds originate from stearic acid, and a carbohydrate-derived thioacetal-alcohol, and their syntheses are potentially general for beta-C-galactosides and their aza-C-partners. They showed potent and specific affinity for gp120 in an assay based on the change of surface pressure when the glycolipid monolayers were exposed to Solutions of gp120. Interestingly, the aza-C-glycoside exhibited a significantly higher affinity than GalCer, whereas the C-glycoside was as active as GalCer. (c) 2005 Elsevier Ltd. All rights reserved.