benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-β-L-arabinopyranoside | 115983-63-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-β-L-arabinopyranoside
• 英文别名: (2S,3R,4R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-methyl-2-phenylmethoxyoxan-4-ol
• CAS: 115983-63-6
• 化学式: C₁₉H₃₂O₄Si
• 分子量: 352.546
• InChiKey: TYJPQNVRXPXNGL-SPUZQDLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-β-L-arabinopyranoside 在 吡啶 、 4-吡咯烷基吡啶 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 Acetic acid (2S,3R,4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-hexyl ester
  参考文献：
  名称：

  Organoaluminum-induced opening of the pyranosidic ring of benzyl 2-deoxy-2-C-methylpentopyranosides

  摘要：

  DOI：

  10.1021/jo00284a028
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.83h， 生成 benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-β-L-arabinopyranoside
  参考文献：
  名称：

  Regioselective and stereoselective oxirane ring-openings of 2,3-anhydropentopyranosides with some methyl-group donating organometallic reagents

  摘要：

  DOI：

  10.1021/jo00254a023

文献信息

• Organotitanium-induced stereoselective alkylative endo-cleavage of benzyl pentopyranosides
  作者：Roger Olsson、Pontus Rundström、Björn Persson、Torbjörn Frejd

  DOI：10.1016/s0008-6215(97)10079-9

  日期：1998.2

  The results presented are the first examples where organotitanium reagents induced alkylative endo-cleavage of carbohydrates. The best conditions for the alkylative transfer of a methyl group to benzyl 2-deoxy-2- C-methyl-4-O-(tert-butyldimethylsilyl)-alpha-D-arabinopyranoside (1) were the application of one equivalent of AlMe3 followed by four equivalents of MeTiCl3 generated by mixing TiCl4 and ZnMe2 in a ratio 2:1, or, alternatively, treatment of 1 with two equivalents of 1:1 Me2TiCl2-ZnMe2. Both the yields and diastereoselectivities were comparable with those of the reaction with AlMe3 but the titanium reagents were more reactive and could be applied at much lower temperatures than the aluminium reagent. (C) 1998 Elsevier Science Ltd. All rights reserved.
• INGHARDT, TORD;FREJD, TORBJORN, J. ORG. CHEM., 54,(1989) N3, C. 5539-5543
  作者：INGHARDT, TORD、FREJD, TORBJORN

  DOI：——

  日期：——
• INGHARDT, TORD;FREJD, TORBJORN;MAGNUSSON, GORAN, J. ORG. CHEM., 53,(1988) N 19, C. 4542-4548
  作者：INGHARDT, TORD、FREJD, TORBJORN、MAGNUSSON, GORAN

  DOI：——

  日期：——