(3S,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-{(4S,5R)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-dihydro-furan-2-one | 175911-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-{(4S,5R)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-dihydro-furan-2-one
• 英文别名: (3S,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[(4S,5R)-5-[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-2-one
• CAS: 175911-91-8
• 化学式: C₂₉H₆₀O₈Si₃
• 分子量: 621.047
• InChiKey: WRUBQQPXUZDTRA-YWIRWFRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-{(4S,5R)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-dihydro-furan-2-one 在 吡啶 、 sodium azide 、 氧化汞红 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 生成 (3S,4R,5R)-5-{(4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-dihydro-furan-2-one
  参考文献：
  名称：

  Synthesis of casuarines [pentahydroxylated pyrrolizidines] by sodium hydrogen telluride-induced cyclisations of azidodimesylates

  摘要：

  The key step in the synthesis of four diastereomers of casuarine from eight carbon sugar lactones is the efficient reduction of open chain azidodimesylates by sodium hydrogen telluride [Suzuki-Takaoka reduction] to allow the formation of the pyrrolizidine nucleus by bicyclisation. This is the first report of the synthesis of such highly oxygenated pyrrolizidines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01306-3
• 作为产物：
  描述：

  (3S,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-dihydro-furan-2-one 在 咪唑 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成 (3S,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-{(4S,5R)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-dihydro-furan-2-one
  参考文献：
  名称：

  Acetonides of octonolactones

  摘要：

  Acetonides of the eight carbon sugar lactones, D-erythro-L-talooctono-1, 4-lactone and D-erythro-L-galactooctono-1 4-lactone, readily derived from glucoheptonolactone, are easily accessible intermediates for the synthesis of sugar mimics with six adjacent stereogenic centres and eight contiguous carbon atoms bearing functional groups.

  DOI：

  10.1016/0957-4166(96)00043-2

文献信息

• Caesium Trifluoroacetate Displacement of Triflates in the Inversion of Alcohols
  作者：Andrew Bell、Lea Pickering、Malcolm Finn、Carmen de la Fuente、Thomas Krülle、Benjamin Davis、G. Fleet

  DOI：10.1055/s-1997-1541

  日期：1997.9

  Caesium trifluoroacetate has advantages over both sodium trifluoroacetate and caesium acetate for the efficient inversion of configuration of alcohols by displacement of triflates.

  与三氟乙酸钠和醋酸铯相比，三氟乙酸铯在通过置换三氟酸盐来有效反转醇的构型方面具有优势。