1,2,3,6,2',3',4',6'-octa-O-trimethylsilyl-β-melibiose | 32590-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,6,2',3',4',6'-octa-O-trimethylsilyl-β-melibiose
• 英文别名: TMS(-2)[TMS(-3)][TMS(-4)][TMS(-6)]Gal(a1-6)[TMS(-2)][TMS(-3)][TMS(-4)]Glc(b)-O-TMS；trimethyl-[(2S,3R,4S,5S,6R)-2-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis(trimethylsilyloxy)oxan-2-yl]methoxy]-3,5-bis(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-4-yl]oxysilane
• CAS: 32590-20-8
• 化学式: C₃₆H₈₆O₁₁Si₈
• 分子量: 919.756
• InChiKey: SWPQHIFGBMZXPV-RCGFMNEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.48
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 蜜二糖 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 1,2,3,6,2',3',4',6'-octa-O-trimethylsilyl-α-melibiose 、 1,2,3,6,2',3',4',6'-octa-O-trimethylsilyl-β-melibiose
  参考文献：
  名称：

  Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides

  摘要：

  [GRAPHICS]Reported herein is a general method for the efficient syntheses of a variety of beta -cyano glycosides through the activation of per-O-trimethylsllyl glycosides with TMSI to form alpha -glycosyl iodides, which undergo S(N)2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)(6) in THF/H2O to give the corresponding aminomethyl glycosides.

  DOI：

  10.1021/ol0160405

文献信息

• Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-<i>O</i>-silylated Mono- and Disaccharides
  作者：Abhijit S. Bhat、Jacquelyn Gervay-Hague

  DOI：10.1021/ol0160405

  日期：2001.6.1

  [GRAPHICS]Reported herein is a general method for the efficient syntheses of a variety of beta -cyano glycosides through the activation of per-O-trimethylsllyl glycosides with TMSI to form alpha -glycosyl iodides, which undergo S(N)2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)(6) in THF/H2O to give the corresponding aminomethyl glycosides.