1,4-anhydro-2-deoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-D-erythro-pent-1-enitol | 96760-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 1,4-anhydro-2-deoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-D-erythro-pent-1-enitol
• 英文别名: (2R,3S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,3-dihydrofuran-3-ol
• CAS: 96760-92-8
• 化学式: C₁₁H₂₂O₃Si
• 分子量: 230.379
• InChiKey: UHHRNZMLENNIIS-VHSXEESVSA-N

物化性质

• 沸点：
  275.4±40.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2-deoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-D-erythro-pent-1-enitol 在 palladium diacetate 1,3-双(二苯基膦)丙烷 、 四丁基氟化铵 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.0h， 生成 6-[(2R,5R)-5-(hydroxymethyl)-4-(methoxymethoxy)-2,5-dihydrofuran-2-yl]-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),5,8-tetraen-4-one
  参考文献：
  名称：

  Synthesis of a Novel Coumarin C-Riboside as a Photophysical Probe of Oligonucleotide Dynamics

  摘要：

  DOI：

  10.1021/jo980478+
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 硫酸氢铵 、 六甲基二硅氮烷 作用下， 反应 4.0h， 以74%的产率得到1,4-anhydro-2-deoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-D-erythro-pent-1-enitol
  参考文献：
  名称：

  Facile Preparation of Protected Furanoid Glycals from Thymidine

  摘要：

  The synthesis of O-silyl- and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'-ester and 3- and 5-tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four synthetic steps in overall yields ranging from 17 to 80%.

  DOI：

  10.1021/jo970947s

文献信息

• The [2,3]-Wittig rearrangement route toward annonaceous acetogenins from furanoid glycals: a preliminary study
  作者：P. Bertrand、J.-P. Gesson、B. Renoux、I. Tranoy

  DOI：10.1016/0040-4039(95)00684-5

  日期：1995.6

  The [2,3]-Wittig rearrangement of trimethylsilylpropargyl ethers of furanoid glycals derived from D-mannose and L-gulonic γ-lactone affords cis 2,5-disubstituted dihydrofurans with predominant erythro selectivity. Under the same conditions, [1,2]-Wittig rearrangement is observed with a glycal derived from D-ribonic γ-lactone.

  衍生自D-甘露糖和L-古洛糖酸γ-内酯的呋喃酮糖基的三甲基甲硅烷基炔丙基醚的[2,3] -Wittig重排提供具有主要赤字选择性的顺式2,5-二取代二氢呋喃。在相同条件下，用衍生自D-核糖体γ-内酯的糖基观察到[1,2] -Wittig重排。
• Differentially protected ribofuranoid glycals
  作者：Jane Chi Ya Cheng、Uli Hacksell、G. Doyle Daves

  DOI：10.1021/jo00215a036

  日期：1985.7
• Cyclopropanation and Ring-Expansion of Unsaturated Sugars
  作者：J Hoberg

  DOI：10.1016/00404-0399(50)1387w-

  日期：1995.9.18
• FARR, ROGER N.;DAVES, DOYLE G. (JR.), J. CARBOHYDR. CHEM., 9,(1990) N, C. 653-660
  作者：FARR, ROGER N.、DAVES, DOYLE G. (JR.)

  DOI：——

  日期：——
• Facile Preparation of Protected Furanoid Glycals from Thymidine
  作者：Melissa A. Cameron、Sarah B. Cush、Robert P. Hammer

  DOI：10.1021/jo970947s

  日期：1997.12.1

  The synthesis of O-silyl- and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'-ester and 3- and 5-tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four synthetic steps in overall yields ranging from 17 to 80%.