di-O-benzyl N-[2-(2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetyl]-L-glutamate | 1014698-43-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: di-O-benzyl N-[2-(2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetyl]-L-glutamate
• 英文别名: dibenzyl (2S)-2-[[2-[(2S,3S,4S,5R,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]-2,2-difluoroacetyl]amino]pentanedioate
• CAS: 1014698-43-1
• 化学式: C₆₄H₆₇F₂NO₁₀Si
• 分子量: 1076.32
• InChiKey: BKIUJSKGLFFBKW-IVCNSSJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.47
• 重原子数：
  78
• 可旋转键数：
  28
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  di-O-benzyl N-[2-(2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetyl]-L-glutamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以63%的产率得到
  参考文献：
  名称：

  Synthesis of α-CF₂-mannosides and Their Conversion to Fluorinated Pseudoglycopeptides

  摘要：

  A methodology allowing the synthesis alpha-CF(2)-rnannosides, based on the addition of a difluoroenoxysilane to a glycal followed by a dihydroxylation reaction, is described. The resulting 2,2-difluoro-2-mannosylacetate is converted into two pseudoglycopeptides which may act as E- and P-selectin inhibitors.

  DOI：

  10.1021/jo702466h
• 作为产物：
  描述：

  3,7-anhydro-4,5,6-tri-O-benzyl-8-O-t-butyldiphenylsilyl-2,2-difluoro-D-glycero-D-talo-octosonic acid 、 L-谷氨酸双苄酯对甲苯磺酸盐 在 N-甲基吗啉 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以183 mg的产率得到di-O-benzyl N-[2-(2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetyl]-L-glutamate
  参考文献：
  名称：

  Synthesis of α-CF₂-mannosides and Their Conversion to Fluorinated Pseudoglycopeptides

  摘要：

  A methodology allowing the synthesis alpha-CF(2)-rnannosides, based on the addition of a difluoroenoxysilane to a glycal followed by a dihydroxylation reaction, is described. The resulting 2,2-difluoro-2-mannosylacetate is converted into two pseudoglycopeptides which may act as E- and P-selectin inhibitors.

  DOI：

  10.1021/jo702466h

文献信息

• Synthesis of α-CF₂-mannosides and Their Conversion to Fluorinated Pseudoglycopeptides
  作者：Florent Poulain、Anne-Lise Serre、Jérôme Lalot、Eric Leclerc、Jean-Charles Quirion

  DOI：10.1021/jo702466h

  日期：2008.3.1

  A methodology allowing the synthesis alpha-CF(2)-rnannosides, based on the addition of a difluoroenoxysilane to a glycal followed by a dihydroxylation reaction, is described. The resulting 2,2-difluoro-2-mannosylacetate is converted into two pseudoglycopeptides which may act as E- and P-selectin inhibitors.