phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside | 91510-80-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside
• 英文别名: alpha-D-Ribofuranoside 2,3-O-isopropylidene-1-phenylthio-5-(t-butyldimethylsilyl)-；[(3aR,4R,6R,6aR)-2,2-dimethyl-4-phenylsulfanyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 91510-80-4
• 化学式: C₂₀H₃₂O₄SSi
• 分子量: 396.623
• InChiKey: BVGQTCZBLQDLCG-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside 在 IF₅-pyridine-HF 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 、 2,3-O-isopropylidene-5-O-dimethyl^tbutylsilyl-β-D-ribofuranosyl fluoride
  参考文献：
  名称：

  Synthesis of glycosyl fluorides from (phenylthio)glycosides using IF5–pyridine–HF

  摘要：

  IF5-pyridine-HF, an air- and moisture-stable fluorinating reagent, was applied to the synthesis of glycosyl fluorides from (phenylthio) glycosides. Common protecting groups of alcohol and diol can tolerate the reaction conditions performed, and therefore, the present method is applicable to the synthesis of various glycosyl fluorides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.08.005
• 作为产物：
  描述：

  2,3-O-isopropylidene-5-O-dimethyl-t-butylsiloxy-β-D-ribofuranose 、 二苯二硫醚 在 三乙基膦 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以90%的产率得到phenyl 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-thio-α-D-ribofuranoside
  参考文献：
  名称：

  Fuerstner, Alois, Liebigs Annalen der Chemie, 1993, # 11, p. 1211 - 1218

  摘要：

  DOI：

文献信息

• Two new methods for the synthesis of C-glycosides
  作者：Gary E. Keck、Eric J. Enholm、David F. Kachensky

  DOI：10.1016/s0040-4039(01)90062-0

  日期：1984.1

  Thiophenyl glycosides are converted to C-glycosides by reaction with allyl or methallyltri-n-butylstannane using both “one-electron” and “two-electron” procedures, which give different stereoselectivities in some cases.

  通过使用“单电子”和“双电子”程序，通过与烯丙基或甲基烯丙基三正丁基锡烷反应，将硫代苯基糖苷转化为C-糖苷，在某些情况下，它们提供不同的立体选择性。
• A Synthesis of 1-Lithiated Glycals and 1-Tributylstannyl Glycals from 1-Phenylsulfinyl Glycals via Sulfoxide-Lithium Ligand Exchange
  作者：Philip Kocienski、Krzysztof Jarowicki、Colin Kilner、Zofia Komsta、Jacqueline Milne、Anna Wojtasiewicz、Victoria Coombs

  DOI：10.1055/s-2008-1067226

  日期：2008.9

  1-Lithiated glycals generated by reaction of 1-phenylsulfinyl glycals with either t-BuLi or PhLi are transformed to 1-tributylstannyl glycals on reaction with tributyltin chloride.

  1-苯亚磺酰基缩醛与叔丁基锂或苯基锂反应生成的1-锂化缩醛与三丁基氯化锡反应生成1-三丁基锡化缩醛。
• Fuerstner, Alois, Liebigs Annalen der Chemie, 1993, # 11, p. 1211 - 1218
  作者：Fuerstner, Alois

  DOI：——

  日期：——
• Synthesis of glycosyl fluorides from (phenylthio)glycosides using IF5–pyridine–HF
  作者：Masataka Kunigami、Shoji Hara

  DOI：10.1016/j.carres.2015.08.005

  日期：2015.11

  IF5-pyridine-HF, an air- and moisture-stable fluorinating reagent, was applied to the synthesis of glycosyl fluorides from (phenylthio) glycosides. Common protecting groups of alcohol and diol can tolerate the reaction conditions performed, and therefore, the present method is applicable to the synthesis of various glycosyl fluorides. (C) 2015 Elsevier Ltd. All rights reserved.