allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside | 888958-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside
• 英文别名: Bn(-3)[Bn(-4)]Rha2Ac(a1-2)[Bn(-3)][Bn(-4)]Rha(a1-2)[Bn(-3)][Bn(-4)]Rha(a)-O-allyl；[(2S,3R,4R,5S,6S)-6-methyl-2-[(2S,3R,4R,5S,6S)-6-methyl-2-[(2R,3R,4R,5S,6S)-6-methyl-4,5-bis(phenylmethoxy)-2-prop-2-enoxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)oxan-3-yl] acetate
• CAS: 888958-65-4
• 化学式: C₆₅H₇₄O₁₄
• 分子量: 1079.29
• InChiKey: YWHUGMRTHDXYQR-DIMKQGTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  79
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 25.0h， 生成 propyl α-L-rhamnopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->2)-α-L-rhamnoside
  参考文献：
  名称：

  Synthesis of Glycosyl Phosphates from 1,2-Orthoesters and Application to in Situ Glycosylation Reactions

  摘要：

  A series of glycosyl phosphates were prepared in high yield by treatment of the corresponding 1,2-orthoesters with dibutyl phosphate. Glycosyl phosphates are efficient glycosylating agents even when used in crude form or when generated in situ. The immunodominant epitope trirhamnoside of group B Streptococcus was prepared to demonstrate the synthetic utility of the method.

  DOI：

  10.1021/ol0603155
• 作为产物：
  描述：

  allyl 3,4-di-O-benzyl-α-L-rhamnopyranoside 在 4 A molecular sieve 、 sodium methylate 、 磷酸二丁酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnoside
  参考文献：
  名称：

  Synthesis of Glycosyl Phosphates from 1,2-Orthoesters and Application to in Situ Glycosylation Reactions

  摘要：

  A series of glycosyl phosphates were prepared in high yield by treatment of the corresponding 1,2-orthoesters with dibutyl phosphate. Glycosyl phosphates are efficient glycosylating agents even when used in crude form or when generated in situ. The immunodominant epitope trirhamnoside of group B Streptococcus was prepared to demonstrate the synthetic utility of the method.

  DOI：

  10.1021/ol0603155