(1S,2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]but-3-en-1-ol | 905280-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]but-3-en-1-ol
• CAS: 905280-17-3
• 化学式: C₂₉H₄₀O₄Si
• 分子量: 480.72
• InChiKey: BCFAHNORIQFWSU-MVNQZMKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]but-3-en-1-ol 在 吡啶 、 咪唑 、 sodium hydroxide 、 臭氧 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 [(2R,3S,4R)-2,4-bis[[tert-butyl(diphenyl)silyl]oxymethyl]-5-oxooxolan-3-yl] benzoate
  参考文献：
  名称：

  A simple and stereodivergent strategy for the synthesis of 3′-C-branched 2′,3′-dideoxynucleosides exploiting (Z)-but-2-en-1,4-diol and (R)-2,3-cyclohexylideneglyceraldehyde

  摘要：

  Barbier type additions of allylic bromide 4, derived from (Z)-but-2-en-1,4-diol 2 to (R)-2,3-cyclohexylideneglyceraldehyde 1 were performed through mediation with Zn employing Luche's procedure and also with low valent Cu, Co, and Fe which were produced via bimetal redox strategy in THF to afford 5c,d as the major products. From these, 5a,b were prepared following an oxidation-reduction protocol. Compound 5c was exploited as a representative starting material to develop a simple and inexpensive strategy toward the synthesis of 3'-C-branched 2',3'-dideoxynucleosides having stereodiversity at 3'- and 4'-positions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.120
• 作为产物：
  描述：

  (Z)-4-((tert-butyldiphenylsilyl)oxy)but-2-en-1-ol 在 TEA 、 甲基磺酰氯 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 (1S,2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]but-3-en-1-ol
  参考文献：
  名称：

  A simple and stereodivergent strategy for the synthesis of 3′-C-branched 2′,3′-dideoxynucleosides exploiting (Z)-but-2-en-1,4-diol and (R)-2,3-cyclohexylideneglyceraldehyde

  摘要：

  Barbier type additions of allylic bromide 4, derived from (Z)-but-2-en-1,4-diol 2 to (R)-2,3-cyclohexylideneglyceraldehyde 1 were performed through mediation with Zn employing Luche's procedure and also with low valent Cu, Co, and Fe which were produced via bimetal redox strategy in THF to afford 5c,d as the major products. From these, 5a,b were prepared following an oxidation-reduction protocol. Compound 5c was exploited as a representative starting material to develop a simple and inexpensive strategy toward the synthesis of 3'-C-branched 2',3'-dideoxynucleosides having stereodiversity at 3'- and 4'-positions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.120

文献信息

• A simple and stereodivergent strategy for the synthesis of 3′-C-branched 2′,3′-dideoxynucleosides exploiting (Z)-but-2-en-1,4-diol and (R)-2,3-cyclohexylideneglyceraldehyde
  作者：Angshuman Chattopadhyay、Dibakar Goswami、Bhaskar Dhotare

  DOI：10.1016/j.tetlet.2006.04.120

  日期：2006.7

  Barbier type additions of allylic bromide 4, derived from (Z)-but-2-en-1,4-diol 2 to (R)-2,3-cyclohexylideneglyceraldehyde 1 were performed through mediation with Zn employing Luche's procedure and also with low valent Cu, Co, and Fe which were produced via bimetal redox strategy in THF to afford 5c,d as the major products. From these, 5a,b were prepared following an oxidation-reduction protocol. Compound 5c was exploited as a representative starting material to develop a simple and inexpensive strategy toward the synthesis of 3'-C-branched 2',3'-dideoxynucleosides having stereodiversity at 3'- and 4'-positions. (c) 2006 Elsevier Ltd. All rights reserved.