allyl (3,4,6-tri-O-p-chlorobenzyl-β-D-mannopyranosyl)(1->2)(3,4,6-tri-O-p-chlorobenzyl-β-D-mannopyranosyl)(1->2)(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)(1->2)-3,4,6-tri-O-benzyl-β-D-mannopyranoside | 302799-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl (3,4,6-tri-O-p-chlorobenzyl-β-D-mannopyranosyl)(1->2)(3,4,6-tri-O-p-chlorobenzyl-β-D-mannopyranosyl)(1->2)(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)(1->2)-3,4,6-tri-O-benzyl-β-D-mannopyranoside
• 英文别名: (2S,3S,4R,5R,6R)-2-[(2S,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-2-[(2R,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-enoxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis[(4-chlorophenyl)methoxy]-6-[(4-chlorophenyl)methoxymethyl]oxan-3-yl]oxy-4,5-bis[(4-chlorophenyl)methoxy]-6-[(4-chlorophenyl)methoxymethyl]oxan-3-ol
• CAS: 302799-56-0
• 化学式: C₁₁₁H₁₁₂Cl₆O₂₁
• 分子量: 1994.82
• InChiKey: LBLXXZLZPNESDC-WOQWBMCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.7
• 重原子数：
  138
• 可旋转键数：
  49
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  205
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  allyl (3,4,6-tri-O-p-chlorobenzyl-β-D-mannopyranosyl)(1->2)(3,4,6-tri-O-p-chlorobenzyl-β-D-mannopyranosyl)(1->2)(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)(1->2)-3,4,6-tri-O-benzyl-β-D-mannopyranoside 在 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  合成二糖至六糖1，2-连接的β-甘露聚糖低聚物，末端S连接的四糖同源物和相应的BSA糖缀合物。

  摘要：

  为了研究白色念珠菌细胞壁甘露聚糖的独特免疫学特性，已经合成了（1-> 2）-β-D-甘露吡喃糖基残基的同源低聚物。对氯苄基保护的磺酰溴（2）与空间受阻的参与溶剂新戊酰腈相结合，为合成这些独特的均聚物（从二糖到六糖）提供了一种新方法。糖基供体2在糖基化和随后的还原步骤上均表现出高的非对映选择性，并使合成所需的保护基操纵次数最小化。合成了（1-> 2）-β-D-甘露糖单糖的同源物，其中含有一个末端S-连接的（1-> 2）-β-D-甘露聚糖基。这些化合物的脱保护得到丙基糖苷以及具有氨基封端的糖苷酸系链的低聚物。通过与2-氨基乙硫醇光加成，由寡糖烯丙基糖苷产生系链。通过方格偶联将功能化的半抗原与BSA偶联，并通过TOF质谱确定结合度。

  DOI：

  10.1021/jo010570x
• 作为产物：
  描述：

  三甲基乙腈 、 3,4,6-tri-O-(p-chlorobenzyl)-α-D-arabino-hexopyranos-2-ulosyl bromide 、 allyl (3,4,6-tri-O-p-chlorobenzyl-β-D-mannopyranosyl)(1->2)(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)(1->2)-3,4,6-tri-O-benzyl-β-D-mannopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 silver trifluoromethanesulfonate 、 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到allyl (3,4,6-tri-O-p-chlorobenzyl-β-D-mannopyranosyl)(1->2)(3,4,6-tri-O-p-chlorobenzyl-β-D-mannopyranosyl)(1->2)(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)(1->2)-3,4,6-tri-O-benzyl-β-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a β1,2-Mannopyranosyl Tetrasaccharide Found in the Phosphomannan Antigen of Candida albicans

  摘要：

  [GRAPHICS]The synthesis of a portion of the challenging beta 1,2-mannosyl polymer found in the cell walls of Candida albicans was undertaken to develop a conjugate vaccine against C. albicans and to facilitate NMR conformational studies of this unique polysaccharide. The novel approach to the synthesis of tetrasaccharide 1 employed the modified ulosyl bromide 11 as the glycosyl donor which provided high diastereoselectivity. A participating solvent as well as p-chlorobenzyl protection facilitated the new approach.

  DOI：

  10.1021/ol0061743

文献信息

• Synthesis of Di- to Hexasaccharide 1,2-Linked β-Mannopyranan Oligomers, a Terminal S-Linked Tetrasaccharide Congener and the Corresponding BSA Glycoconjugates
  作者：Mark Nitz、David R. Bundle

  DOI：10.1021/jo010570x

  日期：2001.12.1

  nosyl residue. Deprotection of these compounds afforded the propyl glycosides as well as oligomers with amino terminated aglyconic tethers. The tethers were generated from the oligosaccharide allyl glycosides by photoaddition with 2-aminoethanethiol. The functionalized haptens were coupled to BSA via squarate conjugation, and the degree of incorporation was established by TOF mass spectrometry.

  为了研究白色念珠菌细胞壁甘露聚糖的独特免疫学特性，已经合成了（1-> 2）-β-D-甘露吡喃糖基残基的同源低聚物。对氯苄基保护的磺酰溴（2）与空间受阻的参与溶剂新戊酰腈相结合，为合成这些独特的均聚物（从二糖到六糖）提供了一种新方法。糖基供体2在糖基化和随后的还原步骤上均表现出高的非对映选择性，并使合成所需的保护基操纵次数最小化。合成了（1-> 2）-β-D-甘露糖单糖的同源物，其中含有一个末端S-连接的（1-> 2）-β-D-甘露聚糖基。这些化合物的脱保护得到丙基糖苷以及具有氨基封端的糖苷酸系链的低聚物。通过与2-氨基乙硫醇光加成，由寡糖烯丙基糖苷产生系链。通过方格偶联将功能化的半抗原与BSA偶联，并通过TOF质谱确定结合度。
• Synthesis of a β1,2-Mannopyranosyl Tetrasaccharide Found in the Phosphomannan Antigen of <i>Candida </i><i>albicans</i>
  作者：Mark Nitz、Byron W. Purse、David R. Bundle

  DOI：10.1021/ol0061743

  日期：2000.9.1

  [GRAPHICS]The synthesis of a portion of the challenging beta 1,2-mannosyl polymer found in the cell walls of Candida albicans was undertaken to develop a conjugate vaccine against C. albicans and to facilitate NMR conformational studies of this unique polysaccharide. The novel approach to the synthesis of tetrasaccharide 1 employed the modified ulosyl bromide 11 as the glycosyl donor which provided high diastereoselectivity. A participating solvent as well as p-chlorobenzyl protection facilitated the new approach.