(1S,2S,3S)-1,2-dibenzyloxy-3-tert-butyldimethylsilylcyclohex-4-ene | 200868-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,3S)-1,2-dibenzyloxy-3-tert-butyldimethylsilylcyclohex-4-ene
• 英文别名: [(1S,5S,6S)-5,6-bis(phenylmethoxy)cyclohex-2-en-1-yl]-tert-butyl-dimethylsilane
• CAS: 200868-50-4
• 化学式: C₂₆H₃₆O₂Si
• 分子量: 408.656
• InChiKey: OBDYTOVXOWSVQG-SDHOMARFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.0
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S)-1,2-dibenzyloxy-3-tert-butyldimethylsilylcyclohex-4-ene 在 N-溴代丁二酰亚胺(NBS) 、 叔丁基锂 、 diethylzinc 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 ((1R,4R,5S)-4,5-Bis-benzyloxy-cyclohex-2-enylmethyl)-dimethyl-phenyl-silane
  参考文献：
  名称：

  Synthesis of pseudo-sugars based on desymmetrization of dienylsilanes

  摘要：

  A synthesis of pseudo-sugars using the desymmetrization of a dienylsilane, followed by a stereocontrolled introduction of the hydroxymethyl group at C5. is described. The CH2OH group at C5 was elaborated using either a regioselective cyclopropane-ring opening or a [2,3]-Wittig rearrangement. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10388-4
• 作为产物：
  描述：

  二甲基苯基(叔丁基)硅烷 在 (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan) 、 potassium dioxotetrahydroxoosmate(VI) 、 氨 、 lithium 、 sodium hydride 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 30.0h， 生成 (1S,2S,3S)-1,2-dibenzyloxy-3-tert-butyldimethylsilylcyclohex-4-ene
  参考文献：
  名称：

  Synthesis of pseudo-sugars based on desymmetrization of dienylsilanes

  摘要：

  A synthesis of pseudo-sugars using the desymmetrization of a dienylsilane, followed by a stereocontrolled introduction of the hydroxymethyl group at C5. is described. The CH2OH group at C5 was elaborated using either a regioselective cyclopropane-ring opening or a [2,3]-Wittig rearrangement. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10388-4

文献信息

• Synthesis of pseudo-sugars based on desymmetrization of dienylsilanes
  作者：Rémy Angelaud、Yannick Landais

  DOI：10.1016/s0040-4039(97)10388-4

  日期：1997.12

  A synthesis of pseudo-sugars using the desymmetrization of a dienylsilane, followed by a stereocontrolled introduction of the hydroxymethyl group at C5. is described. The CH2OH group at C5 was elaborated using either a regioselective cyclopropane-ring opening or a [2,3]-Wittig rearrangement. (C) 1997 Elsevier Science Ltd.
• Stereocontrolled access to Carba-C-disaccharides via functionalized dienylsilanes
  作者：Rémy Angelaud、Yannick Landais、Liliana Parra-Rapado

  DOI：10.1016/s0040-4039(97)10389-6

  日期：1997.12

  We report here the total synthesis of a class of Cl --> C6 Carba-C-disaccharide, formed by the association between a 2-deoxyglucose as the sugar unit and a pseudo-pyranose or a pseudo-furanose as the carba-sugar moiety. The carba-sugar fragments were assembled from the corresponding dienylsilanes through a dihydroxylation-cyclopropanation sequence. (C) 1997 Elsevier Science Ltd.
• Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics
  作者：Rémy Angelaud、Odile Babot、Trevor Charvat、Yannick Landais

  DOI：10.1021/jo991225z

  日期：1999.12.1

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.
• Landais, Yannick, Chimia, 1998, vol. 52, # 3, p. 104 - 111
  作者：Landais, Yannick

  DOI：——

  日期：——