allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside | 167013-77-6

• 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-rhamnopyranoside
• 英文别名: Allyl (2-O-acetyl-3,4-di-O-benzyl-alpha-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-alpha-L-rhamnopyranoside；[(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] acetate
• CAS: 167013-77-6
• 化学式: C₄₅H₅₂O₁₀
• 分子量: 752.902
• InChiKey: RHUQEUMPCBLSMA-CKXCRCTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  55
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

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-rhamnopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到allyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  嵌段途径的O-特异性多糖的片段志贺氏菌˚F lexneri血清型2A：支链重复单元的二聚体的一个十糖代表汇集合成1

  摘要：

  的d “甲”乙“ （E ” ）C ' DAB（E）C十糖代表的二聚物的帧偏移的五糖重复的O-特异性多糖的单元弗氏志贺菌2a中被冷凝合成作为它的甲基糖苷五糖给体（d '甲'乙' （E ' ）C “）和五糖受体（DAB（E）C -OMe）。通往这两个构建块的多条融合路线，涉及AB链接或BC链接作为断开位置，与线性策略相比进行了评估。后者是优选的。它基于三氯乙酰亚胺酸化学的使用。设计目标支链低聚糖，以探测保护性单克隆抗体在天然多糖分子水平上的识别。

  DOI：

  10.1021/jo035125b
• 作为产物：
  描述：

  allyl 3,4-di-O-benzyl-α-L-rhamnopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 potassium tert-butylate 、 sodium hydride 作用下， 反应 6.17h， 生成 allyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Studies on carbohydrates XVIII. Synthesis of tetrasaccharide corresponding to biological repeat units of Serratia marcescens O18 polysaccharide

  摘要：

  The sqnthesis of a blocked tetrasaccharide portion of the biological repeat unit, [-->2)L-Rhap alpha(1-->2)L-Rhap alpha(1-->2)L-Rhap alpha (1-->6)D-GlcNAcp alpha(1-->], of the Serratia marcescens O18 polysaccharide was described The key intermediate compounds was 3,4-blocked -L-rhamnose. All compounds were confirmed by use of high resolution NMR and FAB-MS techniques.

  DOI：

  10.1016/s0957-4166(00)86306-5

文献信息

• Glycoconjugates and Their Use as Potential Vaccines Against Infection by Shigella Flexneri
  申请人：Phalipon Armelle

  公开号：US20080112951A1

  公开（公告）日：2008-05-15

  A conjugate molecule comprising an oligo- or polysaccharide covalently bound to a carrier and its use as potential vaccine against infection by S. Flexneri.

  一种共轭分子，包括寡糖或多糖与载体共价结合，并用作潜在的针对S. Flexneri感染的疫苗。
• Glycoconjugates and their use as potential vaccines against infection by Shigella flexneri
  申请人：INSERM (Institut National de la Sante et de la Recherche Medicale)

  公开号：US08124380B2

  公开（公告）日：2012-02-28

  A conjugate molecule comprising an oligo- or polysaccharide covalently bound to a carrier and its use as potential vaccine against infection by S. Flexneri.

  一种共轭分子，包括寡糖或多糖与载体共价结合，可用作潜在的针对S.Flexneri感染的疫苗。
• GLYCOCONJUGATES AND THEIR USE AS POTENTIAL VACCINES AGAINST INFECTION BY SHIGELLA FLEXNERI
  申请人：PHALIPON Armelle

  公开号：US20140161793A2

  公开（公告）日：2014-06-12

  A conjugate molecule comprising an oligo- or polysaccharide covalently bound to a carrier and its use as potential vaccine against infection by S. Flexneri.

  一种共轭分子，包括寡糖或多糖共价结合到载体上，并作为潜在的针对S. Flexneri感染的疫苗使用。
• Synthesis of Glycosyl Phosphates from 1,2-Orthoesters and Application to in Situ Glycosylation Reactions
  作者：Alessandra Ravidà、Xinyu Liu、Linda Kovacs、Peter H. Seeberger

  DOI：10.1021/ol0603155

  日期：2006.4.1

  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.