2-(trimethylsilyl)ethyl 6,2'-O-methylidene-4-O-α-D-galactropyranosyl-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 6,2'-O-methylidene-4-O-α-D-galactropyranosyl-β-D-galactopyranoside
• 英文别名: (1R,3R,5R,6R,7S,8R,13R,15R,16R,17R)-5-(hydroxymethyl)-15-(2-trimethylsilylethoxy)-2,4,9,11,14-pentaoxatricyclo[11.4.0.03,8]heptadecane-6,7,16,17-tetrol
• 化学式: C₁₈H₃₄O₁₁Si
• 分子量: 454.547
• InChiKey: ATWYNVQQKZRBLR-HGTSRWOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.01
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 N-碘代丁二酰亚胺 、 molecular sieve 、 三氟甲磺酸 、 3 A molecular sieve 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 hydrochloric acid diethyl ether 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， -45.0~25.0 ℃ 、101.33 kPa 条件下， 反应 8.8h， 生成 2-(trimethylsilyl)ethyl 6,2'-O-methylidene-4-O-α-D-galactropyranosyl-β-D-galactopyranoside
  参考文献：
  名称：

  Restriction of Conformation in Galabiosides Via an O⁶−O²‘-Methylene Bridge

  摘要：

  Treatment of 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside (12) and 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-beta-D-glucopyranoside (15) with the novel reagent combination formaldehyde diphenylmercaptal-N-iodosuccinimide-trifluoromethanesulfonic acid [(PhS)(2)CH2/NIS/TfOH], gave the corresponding 6,2'-O- and 4,6-O-methylidene acetals 13 and 16 in 52% and 53% yield, respectively. Deacetylation of 13 gave 2-(trimethylsilyl)ethyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (1). The conformation of 1 was similar to that of the non-acetalated parent glycoside.

  DOI：

  10.1021/jo962371x

文献信息

• Restriction of Conformation in Galabiosides Via an <i>O</i>⁶−<i>O</i>²‘-Methylene Bridge
  作者：Michael Wilstermann、Joakim Balogh、Göran Magnusson

  DOI：10.1021/jo962371x

  日期：1997.5.1

  Treatment of 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside (12) and 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-beta-D-glucopyranoside (15) with the novel reagent combination formaldehyde diphenylmercaptal-N-iodosuccinimide-trifluoromethanesulfonic acid [(PhS)(2)CH2/NIS/TfOH], gave the corresponding 6,2'-O- and 4,6-O-methylidene acetals 13 and 16 in 52% and 53% yield, respectively. Deacetylation of 13 gave 2-(trimethylsilyl)ethyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (1). The conformation of 1 was similar to that of the non-acetalated parent glycoside.