(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-4,5-二羟基-6-(羟基甲基)-2-甲氧基四氢吡喃-3-基]氧基-6-甲基四氢吡喃-3,4,5-三醇 | 128962-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-4,5-二羟基-6-(羟基甲基)-2-甲氧基四氢吡喃-3-基]氧基-6-甲基四氢吡喃-3,4,5-三醇
• 英文名称: methyl α-L-rhamnopyranosyl-(1-2)-β-D-galactopyranoside
• 英文别名: methyl 2-O-α-L-rhamnopyranosyl-β-D-galactopyranoside；α-L-Rhap-(1-2)-β-D-Galp-OMe；Methyl 2-O-alpha-rhamnopyranosyl-beta-galactopyranoside；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 128962-66-3
• 化学式: C₁₃H₂₄O₁₀
• 分子量: 340.328
• InChiKey: ZUPSABSQBFCIOU-JSHOUVFRSA-N

物化性质

• 沸点：
  588.2±50.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 氢氧化钾 、 palladium on activated charcoal 、 3 A molecular sieve 、 四乙基溴化铵 、 氢气 、 氰化汞 、 二正丁基氧化锡 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 25.0~85.0 ℃ 、1.6 kPa 条件下， 反应 27.5h， 生成 (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-4,5-二羟基-6-(羟基甲基)-2-甲氧基四氢吡喃-3-基]氧基-6-甲基四氢吡喃-3,4,5-三醇
  参考文献：
  名称：

  Synthesis of di- and tri-saccharides related to the polysaccharide from Streptococcus pneumoniae type 23 and a study of their inhibition in the precipitin reaction

  摘要：

  Syntheses of methyl 2-O-beta-L-rhamnopyranosyl-beta-D-galactopyranoside (9), methyl 2-O-alpha-L-rhamnopyranosyl-beta-D-galactopyranoside (13), and methyl 4-O-beta-D-glucopyranosyl-2-O-alpha-L-rhamnopyranosyl-beta-D- galactopyranoside (16) in good yields are described. Both 13 and 16 significantly inhibit antigen-antibody precipitation in the S. pneumoniae Type 23 immune system. The results indicate that the rhamnosyl group in the side chain of the repeating unit of the antigen is alpha and not beta as reported previously, and that the trisaccharide related to 16 is the immunodominant group.

  DOI：

  10.1016/0008-6215(90)84132-e

文献信息

• Synthesis of a core disaccharide from the Streptococcus pneumoniae type 23F capsular polysaccharide antigen
  作者：Somnath Dasgupta、Mark Nitz

  DOI：10.1016/j.carres.2010.08.002

  日期：2010.10

  The synthesis of methyl alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-galactopyranoside and methyl alpha-L-rhamnopyranosyl-(1 -> 2)-3-(glycer-2-yl-phosphate)-beta-D-galactopyranoside disaccharides from the Streptococcus pneumoniae type 23F capsular polysaccharide is reported. A simple protecting group strategy was followed using commercially available monosaccharides and phosphorylating reagents. H-Phosphonate and phosphoramidite coupling chemistries were explored for introducing the phosphodiester. Hydrazine hydrate was found to be a mild and efficient deacetylating agent, which was required to avoid phosphate migration during the deprotection of the phosphodiester functionalized disaccharide. (C) 2010 Elsevier Ltd. All rights reserved.