1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-2,3,5-tri-O-benzyl-D-ribofuranose | 96689-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-2,3,5-tri-O-benzyl-D-ribofuranose
• 英文别名: (2R,3R,4S,5S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-(2,4,6-trimethoxyphenyl)oxolane
• CAS: 96689-89-3
• 化学式: C₃₅H₃₈O₇
• 分子量: 570.683
• InChiKey: PIBWJKCPFYASMB-KIPVPBBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-2,3,5-tri-O-benzyl-D-ribofuranose 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以21%的产率得到β-1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-D-ribofuranose
  参考文献：
  名称：

  C-Glycosidation of pyridyl thioglycosides

  摘要：

  DOI：

  10.1021/ja00300a036
• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃核糖 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 7.0h， 生成 1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-2,3,5-tri-O-benzyl-D-ribofuranose
  参考文献：
  名称：

  Strategic approach to C-nucleosidesvia sugar anomeric radical, cation, and anion with sugar tellurides

  摘要：

  Direct coupling reactions of the protected D-ribofuranosyl p-anisyl telluride and 2-deoxy-D-ribofuranosyl p-anisyl telluride with electron-poor heteroaromatics and electron-rich aromatics via anomeric radical, cation, and anion were carried out. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01196-9

文献信息

• Surfactant-Type Brønsted Acid Catalyzed Dehydrative Nucleophilic Substitutions of Alcohols in Water
  作者：Seiji Shirakawa、Shū Kobayashi

  DOI：10.1021/ol062813j

  日期：2007.1.1

  A protocol for the dehydrative nucleophilic substitution of benzyl alcohols with a variety of carbon- and heteroatom-centered nucleophiles using dodecylbenzenesulfonic acid (DBSA) as a surfactant-type Bronsted acid catalyst in water has been developed. The reaction system can be applied to the stereoselective C-glycosylation of 1-hydroxy sugars in water. [reaction: see text].

  已经开发出使用十二烷基苯磺酸（DBSA）作为水中的表面活性剂型布朗斯台德酸催化剂，用多种以碳原子和杂原子为中心的亲核试剂对苯甲醇进行脱水亲核取代的方案。该反应系统可以应用于水中1-羟基糖的立体选择性C-糖基化。[反应：请参见文字]。
• An Efficient Glycosylation Reaction of 1-Hydroxy Sugars with Various Nucleophiles Using A Catalytic Amount of Activator and Hexamethyldisiloxane
  作者：Teruaki Mukaiyama、Koki Matsubara、Miyuki Hora

  DOI：10.1055/s-1994-25695

  日期：——

  In the presence of hexamethyldisiloxane and anhydrous calcium sulfate, a catalytic amount of activator such as tin(II) trifluoromethanesulfonate, ytterbium trifluoromethanesulfonate , lanthanum trifluoromethanesulfonate or tin(II) chloride smoothly promotes the glycosylation reactions between 1-hydroxy sugars and free alcohols, electron-rich aromatic compounds or silylated nucleophiles to produce various O -, C - or N - glycosides stereoselectively in high yields. In the case of oxygen or nitrogen nucleophiles, β-ribosides are formed, except that α-ribosides are obtained predominantly in the presence of lithium perchlorate. In the case of carbon nucleophiles such as electron-rich aromatic compounds or silyl enol ethers derived from carbonyl compounds, perfect β-selectivity is shown either in the the presence or absence of lithium perchlorate. Further, pyranosyl substrates such as glucose or galactose afford the corresponding α-anomers, except with electron-rich aromatic compounds.

  在六甲基二硅氧烷和无水硫酸钙的存在下，以催化量的活化剂（如二氟三氟甲磺酸锡、三氟三氟甲磺酸镱、三氟三氟甲磺酸镧或二氯化锡）顺利促进1-羟基糖与自由醇、富电子芳香化合物或硅化亲核试剂之间的糖基化反应，高产率地选择性合成各种O-、C-或N-糖苷。对于氧或氮亲核试剂，主要生成β-核糖苷，但在高氯酸锂存在下主要得到α-核糖苷。对于碳亲核试剂（如富电子芳香化合物或来自羰基化合物的硅基烯醇醚），无论在高氯酸锂存在或不存在下，均表现出完全的β-选择性。此外，吡喃糖基底物（如葡萄糖或半乳糖）主要生成相应的α-异构体，但对于富电子芳香化合物则例外。
• He, Wei; Togo, Hideo; Waki, Yuji, Journal of the Chemical Society. Perkin transactions I, 1998, # 15, p. 2425 - 2433
  作者：He, Wei、Togo, Hideo、Waki, Yuji、Yokoyama, Masataka

  DOI：——

  日期：——
• C-Glycosidation of pyridyl thioglycosides
  作者：Andrew O. Stewart、Robert M. Williams

  DOI：10.1021/ja00300a036

  日期：1985.7
• Strategic approach to C-nucleosidesvia sugar anomeric radical, cation, and anion with sugar tellurides
  作者：Wei He、Hideo Togo、Masataka Yokoyama

  DOI：10.1016/s0040-4039(97)01196-9

  日期：1997.8

  Direct coupling reactions of the protected D-ribofuranosyl p-anisyl telluride and 2-deoxy-D-ribofuranosyl p-anisyl telluride with electron-poor heteroaromatics and electron-rich aromatics via anomeric radical, cation, and anion were carried out. (C) 1997 Elsevier Science Ltd.