1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-C-(oct-1-ynyl)-α-D-ribofuranose | 896130-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-C-(oct-1-ynyl)-α-D-ribofuranose
• 英文别名: (3aR,5R,6R,6aR)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-6-oct-1-ynyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 896130-09-9
• 化学式: C₂₂H₄₀O₅Si
• 分子量: 412.642
• InChiKey: AOSGNCLDDIRUAN-VQQMMKBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-C-(oct-1-ynyl)-α-D-ribofuranose 在 甲醇 、 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 (cyclooctadienyl)(cyclopentadienyl)ruthenium chloride 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 水 、 sodium methylate 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 22.33h， 生成 1-[(2'R,3S,3'R,5'R)-4-hexyl-3'-hydroxy-5'-(hydroxymethyl)spiro[1H-2-benzofuran-3,4'-oxolane]-2'-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  目标兼具灵活性：合成C（3 '）-螺旋型核苷

  摘要：

  我们报告了一个简单的策略，用于合成以（2 + 2 + 2）-环三聚为关键反应的C（3'）-螺二氢异苯并呋喃核苷的集合。环三聚反应容易与具有二炔单元的未保护的核苷一起进行。当二炔的两个炔都是末端时，区域选择性差。然而，当末端炔烃之一被另外取代时，环三聚是高度非对映选择性的。由于关键的双环环化是最后一步，因此该策略在炔烃方面提供了灵活性，因此适合合成聚焦的小分子文库。

  DOI：

  10.1016/j.tetlet.2011.06.100
• 作为产物：
  描述：

  1-辛炔 、 5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.0h， 以88%的产率得到1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-C-(oct-1-ynyl)-α-D-ribofuranose
  参考文献：
  名称：

  The influence of electronic factors on palladium-mediated cycloisomerization: a systematic investigation of competitive 5-exo-dig versus 6-endo-dig cyclizations of sugar alkynols

  摘要：

  Pd-mediated cycloisomerization of 3-C-alkynyl-allo- and ribofuranose derivatives was investigated in detail to understand the influence of electronic factors on the regioselectivity in ring closure reaction. The reactions in general are influenced by the electronic nature of the substituent on the alkyne unit. A preference for endo-dig cyclization over exo-dig is noted, if the alkynyl substituent is not sufficiently electron withdrawing, (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.072

文献信息

• Palladium mediated cycloisomerization of sugar alkynols: synthesis of cyclic enol-ethers and spiroketals
  作者：C.V. Ramana、Rosy Mallik、Rajesh G. Gonnade、Mukund K. Gurjar

  DOI：10.1016/j.tetlet.2006.03.143

  日期：2006.5

  Functionalized bicyclic enol-ethers and spiroketals are prepared by Pd catalyzed cycloisomerization of 3-C-alkynylfuranosyl derivatives. Cycloisomerization of differently substituted alkyne derivatives revealed a preference for 6-endo-dig cyclization over 5-exo-dig if the substituent is not sufficiently electron withdrawing. The scope of these cycloisomerizations has been further extended by integrating with conjugate addition. (c) 2006 Elsevier Ltd. All rights reserved.
• Target cum flexibility: synthesis of C(3′)-spiroannulated nucleosides
  作者：Mangesh P. Dushing、C.V. Ramana

  DOI：10.1016/j.tetlet.2011.06.100

  日期：2011.9

  report a simple strategy for the synthesis of a collection of C(3′)-spirodihydroisobenzo-furannulated nucleosides featuring a [2+2+2]-cyclotrimerization as the key reaction. The cyclotrimerization reactions are facile with the unprotected nucleosides having a diyne unit. When both alkynes of the diyne are terminal, the regioselectivity is poor. However, when one of the terminal alkynes is additionally

  我们报告了一个简单的策略，用于合成以（2 + 2 + 2）-环三聚为关键反应的C（3'）-螺二氢异苯并呋喃核苷的集合。环三聚反应容易与具有二炔单元的未保护的核苷一起进行。当二炔的两个炔都是末端时，区域选择性差。然而，当末端炔烃之一被另外取代时，环三聚是高度非对映选择性的。由于关键的双环环化是最后一步，因此该策略在炔烃方面提供了灵活性，因此适合合成聚焦的小分子文库。
• The influence of electronic factors on palladium-mediated cycloisomerization: a systematic investigation of competitive 5-exo-dig versus 6-endo-dig cyclizations of sugar alkynols
  作者：C.V. Ramana、Rosy Mallik、Rajesh G. Gonnade

  DOI：10.1016/j.tet.2007.10.072

  日期：2008.1

  Pd-mediated cycloisomerization of 3-C-alkynyl-allo- and ribofuranose derivatives was investigated in detail to understand the influence of electronic factors on the regioselectivity in ring closure reaction. The reactions in general are influenced by the electronic nature of the substituent on the alkyne unit. A preference for endo-dig cyclization over exo-dig is noted, if the alkynyl substituent is not sufficiently electron withdrawing, (c) 2007 Elsevier Ltd. All rights reserved.