methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranoside | 460356-05-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranoside
• 英文别名: Rha2Ac3Ac4Ac(a1-3)a-Rha1Me；[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-[(2R,3R,4R,5S,6S)-3,5-dihydroxy-2-methoxy-6-methyloxan-4-yl]oxy-2-methyloxan-3-yl] acetate
• CAS: 460356-05-2
• 化学式: C₁₉H₃₀O₁₂
• 分子量: 450.44
• InChiKey: SXTBHOCOWACFFU-CKBIDTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranoside 在 吡啶 、 甲醇 、 乙酰氯 作用下， 生成 methyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  SYNTHESIS OF A XYLOSYLATED RHAMNOSE PENTASACCHARIDE—THE REPEATING UNIT OF THE O-SPECIFIC SIDE CHAIN OF LIPOPOLYSACCHARIDES FROM THE REFERENCE STRAINS FOR Stenotrophomonas maltophilia SEROGROUP O18

  摘要：

  A xylosylated rhamnose pentasaccharide, alpha-L-Rhap-(1-->3)-[beta-L-Xylp-(1-->2)-] [beta-L-Xylp-(1-->4)-]alpha-L-Rhap-(1-->3)-L-Rhap, the repeating unit of the O-specific side chain of the lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroup O18, was synthesized by a highly regio- and stereoselective procedure. Thus coupling of methyl rhamnopyranoside (9) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl trichloroacetimidate (8) gave the (1-->3)-linked disaccharide (10), and subsequent benzoylation and deacetylation afforded the disaccharide acceptor 12. Condensation of 12 with 8 yielded methyl 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (13). Coupling of 13 with 2,3,4-tri-O-benzoyl-alpha-L-xylopyranosyl trichloroacetimidate (4) followed by deprotection gave the target pentasaccharide (15).

  DOI：

  10.1081/car-120003740
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 在 ammonium hydroxide 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranoside
  参考文献：
  名称：

  SYNTHESIS OF A XYLOSYLATED RHAMNOSE PENTASACCHARIDE—THE REPEATING UNIT OF THE O-SPECIFIC SIDE CHAIN OF LIPOPOLYSACCHARIDES FROM THE REFERENCE STRAINS FOR Stenotrophomonas maltophilia SEROGROUP O18

  摘要：

  A xylosylated rhamnose pentasaccharide, alpha-L-Rhap-(1-->3)-[beta-L-Xylp-(1-->2)-] [beta-L-Xylp-(1-->4)-]alpha-L-Rhap-(1-->3)-L-Rhap, the repeating unit of the O-specific side chain of the lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroup O18, was synthesized by a highly regio- and stereoselective procedure. Thus coupling of methyl rhamnopyranoside (9) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl trichloroacetimidate (8) gave the (1-->3)-linked disaccharide (10), and subsequent benzoylation and deacetylation afforded the disaccharide acceptor 12. Condensation of 12 with 8 yielded methyl 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (13). Coupling of 13 with 2,3,4-tri-O-benzoyl-alpha-L-xylopyranosyl trichloroacetimidate (4) followed by deprotection gave the target pentasaccharide (15).

  DOI：

  10.1081/car-120003740