methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside | 876345-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
• CAS: 876345-19-6
• 化学式: C₄₃H₅₀O₉S
• 分子量: 742.931
• InChiKey: COYAKJAQRHMIQU-YLXDAFQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  53.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-methoxycarbonylpentyl 2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the tetrasaccharide side chain of the major glycoprotein of the Bacillus anthracis exosporium

  摘要：

  An alpha-glycoside of the tetrasaccharide sequence beta-Ant-(1 -> 3)-alpha-L-Rhap-(1 -> 3)-alpha-L-Rhap-(1 -> 2)-alpha-L-Rhap whose aglycon allows conjugation to suitable carriers was synthesized. The NMR characteristics of the compound are virtually identical with those of the alpha-anomer of the tetrasaccharide isolated from the major glycoprotein of the Bacillus anthracis exosporium. Thus, the correct structure of the natural product has been proven by chemical synthesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.056
• 作为产物：
  描述：

  methyl 3-O-acetyl-2,4-di-O-benzyl-6-deoxy-1-thio-α-L-mannopyranoside 在 2,6-di-t-Bu-Me-pyridine 、 silver trifluoromethanesulfonate 、 氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the tetrasaccharide side chain of the major glycoprotein of the Bacillus anthracis exosporium

  摘要：

  An alpha-glycoside of the tetrasaccharide sequence beta-Ant-(1 -> 3)-alpha-L-Rhap-(1 -> 3)-alpha-L-Rhap-(1 -> 2)-alpha-L-Rhap whose aglycon allows conjugation to suitable carriers was synthesized. The NMR characteristics of the compound are virtually identical with those of the alpha-anomer of the tetrasaccharide isolated from the major glycoprotein of the Bacillus anthracis exosporium. Thus, the correct structure of the natural product has been proven by chemical synthesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.056

文献信息

• Immunogens related to the synthetic tetrasaccharide side chain of the Bacillus anthracis exosporium
  作者：Rina Saksena、Roberto Adamo、Pavol Kováč

  DOI：10.1016/j.bmc.2007.03.057

  日期：2007.6

  The known methyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-alpha-L-rhamnopyranoside (3) was converted to the corresponding 5-methoxycarbonylpentyl glycoside 4 which was deacetylated. The product 5 was used as the initial glycosyl acceptor to construct two trirhamnoside glycosyl acceptors having HO-3(III) flanked by either benzoyl or benzyl groups, compounds 10 and 29, respectively [fully protected, except HO-3(III)

  将已知的甲基2-O-乙酰基-3,4-二-O-苄基-1-硫代-α-L-鼠李糖吡喃糖苷（3）转化为相应的5-甲氧基羰基戊基糖苷4，其被去乙酰化。产物5用作起始的糖基受体，以构建两个侧接苯甲酰基或苄基的HO-3（III）的三鼠李糖苷糖基受体，分别是化合物10和29 [除HO-3（III）外，均得到充分保护，α -L-Rha-（1-> 3）-alpha-L-Rha-（1-> 2）-alpha-L-Rha-1-O-（CH2）5COOCH3]。当将它们用乙基4-叠氮基-3-O-苄基-4,6-二脱氧-2-O-溴乙酰基-1-硫代β-D-吡喃葡萄糖苷糖基化时（18），只有苄基化的糖基受体29给出了良好的收率。所需的四糖30。α和β连接的产物，以及相应的原酸酯23，当用带有2-O-溴乙酰基保护基的糖基供体进行10个糖基化时，几乎以相等的量形成α-β。在O-2为30时脱保护，然后进一步使分子官能化并整体脱保护，