tert-butyl-[(2R)-2-[(4S,5S)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]-2-(3-fluorohept-1-en-2-yloxy)ethoxy]-diphenylsilane | 936111-34-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tert-butyl-[(2R)-2-[(4S,5S)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]-2-(3-fluorohept-1-en-2-yloxy)ethoxy]-diphenylsilane
• CAS: 936111-34-1
• 化学式: C₃₆H₄₇FO₄SSi
• 分子量: 622.917
• InChiKey: WCBSHFSHSDMKBA-OYKWTTPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.26
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(2R)-2-[(4S,5S)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]-2-(3-fluorohept-1-en-2-yloxy)ethoxy]-diphenylsilane 在 2,6-二叔丁基-4-甲基吡啶 、 dimethyl sulfide borane 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3aS,4R,6R,7R,7aR)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-[(1R)-1-fluoropentyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
  参考文献：
  名称：

  Synthesis of β-C-galacto-Pyranosides with Fluorine on the Pseudoanomeric Substituent

  摘要：

  beta-C-galacto-Pyranosides with CHF and CF2 substitutes for the glycosidic oxygen were prepared through a four-step sequence starting from a central 1-thio-1,2-O-isopropylidene acetal alcohol and different alpha-fluoro- and alpha,alpha-difluoro acids. The key step in the synthesis is the oxocarbenium cyclization of an intermediate enol ether-thioacetal to a C1-substituted glycal.

  DOI：

  10.1021/ol070169i
• 作为产物：
  描述：

  2-氟己酸 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 生成 tert-butyl-[(2R)-2-[(4S,5S)-2,2-dimethyl-5-phenylsulfanyl-1,3-dioxolan-4-yl]-2-(3-fluorohept-1-en-2-yloxy)ethoxy]-diphenylsilane
  参考文献：
  名称：

  Synthesis of β-C-galacto-Pyranosides with Fluorine on the Pseudoanomeric Substituent

  摘要：

  beta-C-galacto-Pyranosides with CHF and CF2 substitutes for the glycosidic oxygen were prepared through a four-step sequence starting from a central 1-thio-1,2-O-isopropylidene acetal alcohol and different alpha-fluoro- and alpha,alpha-difluoro acids. The key step in the synthesis is the oxocarbenium cyclization of an intermediate enol ether-thioacetal to a C1-substituted glycal.

  DOI：

  10.1021/ol070169i

文献信息

• Synthesis of β-<i>C</i>-<i>galacto</i>-Pyranosides with Fluorine on the Pseudoanomeric Substituent
  作者：Kurissery A. Tony、Richard W. Denton、Anna Dilhas、Jesús Jiménez-Barbero、David R. Mootoo

  DOI：10.1021/ol070169i

  日期：2007.4.1

  beta-C-galacto-Pyranosides with CHF and CF2 substitutes for the glycosidic oxygen were prepared through a four-step sequence starting from a central 1-thio-1,2-O-isopropylidene acetal alcohol and different alpha-fluoro- and alpha,alpha-difluoro acids. The key step in the synthesis is the oxocarbenium cyclization of an intermediate enol ether-thioacetal to a C1-substituted glycal.