methyl 3-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranoside | 128962-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-methoxy-5-[(2S,3R,4R,5S,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-4-phenylmethoxyoxan-3-ol
• CAS: 128962-65-2
• 化学式: C₄₁H₄₈O₁₀
• 分子量: 700.826
• InChiKey: SWPFMGKCZTUKAT-KPLWGOLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  51.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  114.3
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranoside 在 sodium hydroxide 、 palladium on activated charcoal 、 4 A molecular sieve 、 氢气 、 silver trifluoromethanesulfonate 、 四丁基硫酸氢铵 、 1,1,3,3-四甲基脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 60.0h， 生成
  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
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 氢氧化钾 、 3 A molecular sieve 、 四乙基溴化铵 、 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 、 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 methyl 3-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-galactopyranoside
  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

• RAY, ASIM K.;MADDALI, USHA B.;ROY, ABHIJIT;ROY, NIRMOLENDU, CARBOHYDR. RES., 197,(1990) C. 93-100
  作者：RAY, ASIM K.、MADDALI, USHA B.、ROY, ABHIJIT、ROY, NIRMOLENDU

  DOI：——

  日期：——