2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-6,2'-O-methylidene-4-O-(3,4,6-tri-O-acetyl-α-D-galactropyranosyl)-β-D-galactopyranoside | 189744-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-6,2'-O-methylidene-4-O-(3,4,6-tri-O-acetyl-α-D-galactropyranosyl)-β-D-galactopyranoside
• 英文别名: [(1S,3R,5R,6S,7S,8R,13R,15R,16R,17S)-6,7,16,17-tetraacetyloxy-15-(2-trimethylsilylethoxy)-2,4,9,11,14-pentaoxatricyclo[11.4.0.03,8]heptadecan-5-yl]methyl acetate
• CAS: 189744-15-8
• 化学式: C₂₈H₄₄O₁₆Si
• 分子量: 664.733
• InChiKey: VITKRBLEWXTORV-CJBKXDKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  187
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-6,2'-O-methylidene-4-O-(3,4,6-tri-O-acetyl-α-D-galactropyranosyl)-β-D-galactopyranoside 在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 2-bromoethyl 2,3-di-O-acetyl-6,2'-O-methylidene-4-O-(3,4,6-tri-O-acetyl-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
• 作为产物：
  描述：

  2-trimetylsilylethyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranoside 在 palladium on activated charcoal 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 、 hydrochloric acid diethyl ether 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 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 7.3h， 生成 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-6,2'-O-methylidene-4-O-(3,4,6-tri-O-acetyl-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