allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside | 169836-50-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
• 英文别名: allyl 3-O-<2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranosyl>-2,4,6-tri-O-benzyl-α-D-galactopyranoside；allyl 3-O-[2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranosyl]-2,4,6-tri-O-benzyl-α-D-galactopyranoside；Bn(-3)[Bn(-4)][Bn(-6)]Gal2Ac(b1-3)[pivaloyl(-4)][pivaloyl(-6)]GalNAc(b1-3)[Bn(-2)][Bn(-4)][Bn(-6)]Gal(a)-O-allyl；[(2R,3R,4R,5R,6S)-5-acetamido-4-[(2R,3R,4S,5S,6R)-3-acetyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-[(2R,3S,4S,5R,6S)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxan-4-yl]oxy-3-(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 169836-50-4
• 化学式: C₇₇H₉₃NO₁₉
• 分子量: 1336.58
• InChiKey: LHONADKHABIWCS-CQWBWEJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  97
• 可旋转键数：
  37
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  219
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 14.0h， 生成 allyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Improvement of the Synthesis of Immunological Carbohydrate Vaccines Containing the Tumour Associate Antigen CaMBr1

  摘要：

  The simplified synthesis of a portion of Globo-H hexasaccharide, a saccharide antigen overexpressed by breast cancer cells, and its conjugation to two different immunogenic proteins are described, The conjugated vaccines, evaluated in a preclinical model, showed good immunogenic potential.

  DOI：

  10.1002/1099-0690(200111)2001:22<4331::aid-ejoc4331>3.0.co;2-r
• 作为产物：
  描述：

  allyl 3-O-(4-methoxybenzyl)-α-D-galactopyranoside 在 吡啶 、 三氟甲磺酸 、 水 、 sodium methylate 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 14.66h， 生成 allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Improvement of the Synthesis of Immunological Carbohydrate Vaccines Containing the Tumour Associate Antigen CaMBr1

  摘要：

  The simplified synthesis of a portion of Globo-H hexasaccharide, a saccharide antigen overexpressed by breast cancer cells, and its conjugation to two different immunogenic proteins are described, The conjugated vaccines, evaluated in a preclinical model, showed good immunogenic potential.

  DOI：

  10.1002/1099-0690(200111)2001:22<4331::aid-ejoc4331>3.0.co;2-r

文献信息

• Oligosaccharides related to tumor-associate antigens. Part 3. Synthesis of the propyl glycosides of the trisaccharide ?-D-Galp-(1?3)-?-D-GalpNAc-(1?3)-?-D-Galp and of the Tetrasaccharide ?-L-Fucp-(1?2)-?-D-Galp-(1?3)-?-D-GalpNAc-(1?3)-?-D-Galp, components of a tumor antigen recognized by the antibody MBr1
  作者：Luigi Lay、Luigi Panza、Giovanni Russo、Diego Colombo、Fiamma Ronchetti、Elena Adobati、Silvana Canevari

  DOI：10.1002/hlca.19950780302

  日期：1995.5.10

  The synthesis of the trisaccharide β-D-Galp-(13)-β-D-GalpNAc-(13)-α-D-Galp-1-OPr (2) and of the tetrasaccharide α-L-Fucp-(12)-β-D-GalpNAc-(13)-β-D-Galp-1-OPr (3), starting from the disaccharidic dihydrooxazole donor 5, is described. Glycosylation of 5 with 6 in the presence of Me3SiOTf gave the trisaccharide 7 which was deprotected with standard methods to give, via8, compound 2 (Scheme 1). Alternatively

  三糖β-d-Gal的合成p - （13）-β-d-Gal的p NAc-（13）-α-d-Gal的p -1-OPR（2）和四糖α-L-岩藻糖的p - （12）-β-d-Gal的p NAc-（13）-β-d-Gal的p -1-OPR（3）中，从二糖供体二氢恶唑开始5，进行说明。在Me 3 SiOTf存在下将5与6进行糖基化反应，制得三糖7，将其用标准方法脱保护，通过8生成化合物2（流程1）。备选地，将8保护为4'，6'- O-亚苄基衍生物9，随后用10进行糖基化并通过标准脱保护得到四糖3（方案2）。生物测试表明，三糖2不能抑制单克隆抗体MBR1到靶肿瘤细胞MCF7的结合，而四糖3抑制在结合CA。7倍程度相对于先前测试的三糖α-L-岩藻糖p - （12）-β-d-Gal的p - （13）-β-d-Gal的pNAc-1-OPr。这些结果表明，与化合物1的单元D相对应的半乳糖在定义MBr1识别的表​