(2R,3R,4S,5R,6S)-5-Benzyloxy-2-hydroxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3,4-diol | 1053648-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-5-Benzyloxy-2-hydroxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3,4-diol
• 英文别名: 4-Methylphenyl 2-O-benzyl-1-thio-beta-D-galactopyranoside；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(4-methylphenyl)sulfanyl-5-phenylmethoxyoxane-3,4-diol
• CAS: 1053648-41-1
• 化学式: C₂₀H₂₄O₅S
• 分子量: 376.474
• InChiKey: AADUXDHWWGZARF-CXQPBAHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-5-Benzyloxy-2-hydroxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3,4-diol 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 、 三氟化硼乙醚 、 氢气 、 caesium carbonate 、 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 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -45.0~25.0 ℃ 、101.33 kPa 条件下， 反应 29.63h， 生成 2-(octadecylthio)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
• 作为产物：
  描述：

  4-methylphenyl 3,4-O-isoporpylidene-6-O-(2-methoxyisopropyl)-1-thio-β-D-galactopyranoside 在 sodium hydride 、 溶剂黄146 作用下， 反应 6.0h， 生成 (2R,3R,4S,5R,6S)-5-Benzyloxy-2-hydroxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3,4-diol
  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.