(2S,3R,4R,5S)-5-O-benzyl-4-methyl-2-O-(tert-butyldimethylsilyl)-1,2,3,5-hexanetetrol | 122822-17-7

• 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: (2S,3R,4R,5S)-5-O-benzyl-4-methyl-2-O-(tert-butyldimethylsilyl)-1,2,3,5-hexanetetrol
• 英文别名: (2S,3R,4R,5S)-2-[tert-butyl(dimethyl)silyl]oxy-4-methyl-5-phenylmethoxyhexane-1,3-diol
• CAS: 122822-17-7
• 化学式: C₂₀H₃₆O₄Si
• 分子量: 368.589
• InChiKey: GFODUZQFLKERBP-PBWTXFEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S)-5-O-benzyl-4-methyl-2-O-(tert-butyldimethylsilyl)-1,2,3,5-hexanetetrol 生成 [(2S)-2-[tert-butyl(dimethyl)silyl]oxy-2-[(4R,5S,6S)-2,2,5,6-tetramethyl-1,3-dioxan-4-yl]ethyl] acetate
  参考文献：
  名称：

  INGHARDT, TORD;FREJD, TORBJORN, J. ORG. CHEM., 54,(1989) N3, C. 5539-5543

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl 2-deoxy-2-C-methyl-4-O-(tert-butyldimethylsilyl)-β-L-arabinopyranoside 、 三甲基铝 生成 (2S,3R,4R,5S)-5-O-benzyl-4-methyl-2-O-(tert-butyldimethylsilyl)-1,2,3,5-hexanetetrol
  参考文献：
  名称：

  INGHARDT, TORD;FREJD, TORBJORN, J. ORG. CHEM., 54,(1989) N3, C. 5539-5543

  摘要：

  DOI：

文献信息

• Organoaluminium induced ring-opening of epoxypyranosides. IV. Synthesis and structure of γ- hydroxy-lsoleucine stereoisomers and their corresponding lactones.
  作者：Tord Inghardt、Torbjörn Frejd、Göran Svensson

  DOI：10.1016/s0040-4020(01)86574-1

  日期：1991.8

  Two gamma- hydroxy-isoleucine stereoisomers 8 (2R, 3R, 4R), and 14 (2S, 3R, 4R) as well as their corresponding gamma- lactones 9 and 15 were synthesized using a tandem, Me3Al induced opening of the epoxide and pyranoside rings of benzyl 2,3-anhydro-4-O-(tert-butyldimethylsilyl)-beta-L-ribopyranoside (1). The structure of the lactone hydrochloride 9 was confirmed by an X-ray crystal structure determination.
• 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.