methyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside | 460356-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: Rha(a1-3)[Bz(-2)][Bz(-4)]a-Rha1Me；[(2S,3S,4R,5R,6R)-5-benzoyloxy-6-methoxy-2-methyl-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] benzoate
• CAS: 460356-06-3
• 化学式: C₂₇H₃₂O₁₁
• 分子量: 532.544
• InChiKey: GIHYQBAQPPYWBY-IAZKXOFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-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：

  2,3,4-tri-O-acetyl-L-rhamnopyranose 在 吡啶 、 甲醇 、 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 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 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

文献信息

• Efficient synthesis of a heptasaccharide, the repeating unit of the O-chain lipopolysaccharide produced by Xanthomonas campestris strain 642
  作者：Jianjun Zhang、Jun Ning、Fanzuo Kong

  DOI：10.1016/s0008-6215(03)00080-6

  日期：2003.5

  alpha-L-Rhap-(1 --> 3)-alpha-L-Rhap-(1 --> 2)-alpha--L-Rhap-(1 --> 3)-[beta-D-Xylp-(1 --> 2)-][beta-D-Xylp-(1 --> 4)-]alpha-L-Rhap-(1 --> 3)-alpha-L-Rhap, the repeating unit of the O-chain lipopolysaccharide produced by Xanthomonas campestris strain 642 was synthesized as its methyl glycoside via 3-O-selective glycosylation of methyl alpha-L-rhamnopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (9) with 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 2)-3,4-di-O-benzoyl-(alpha-L-rhamnopyranosyl trichloroacetimidate (8), followed by dixylosylation with 2,3,4-tri-O-benzoyl-alpha,beta-D-xylopyranosyl trichloroacetimidate (12) and subsequent deacylation. (C) 2003 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF A XYLOSYLATED RHAMNOSE PENTASACCHARIDE—THE REPEATING UNIT OF THE O-SPECIFIC SIDE CHAIN OF LIPOPOLYSACCHARIDES FROM THE REFERENCE STRAINS FOR <i>Stenotrophomonas maltophilia</i> SEROGROUP O18
  作者：Jianjun Zhang、Fanzuo Kong

  DOI：10.1081/car-120003740

  日期：2002.5.31

  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).