3-(benzyloxycarbonylamino)propyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 726134-69-6

• 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: 3-(benzyloxycarbonylamino)propyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 726134-69-6
• 化学式: C₃₇H₄₉NO₂₀
• 分子量: 827.791
• InChiKey: OQFFSINXYWJPOP-XGGIYNTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  58.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  259.35
• 氢给体数：
  1.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  3-(benzyloxycarbonylamino)propyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Novel Carborane-hybrids Based on a Triazine Scaffold for Boron Neutron Capture Therapy

  摘要：

  三聚氯氰已被用作合成潜在BNCT（硼中子俘获治疗）药物的骨架，这些药物包含一个碳硼烷簇作为亲电部分，一个糖基作为亲水臂，以及一个氨基酸用于与生物活性分子结合；从原理上讲，这种方法特别适合于组合化学方法的运用。

  DOI：

  10.1055/s-2004-822897
• 作为产物：
  描述：

  lactose octaacetate 、 3-(苄氧羰基氨基)-1-丙醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以43%的产率得到3-(benzyloxycarbonylamino)propyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  α-Gal五糖的四组分一锅法合成。

  摘要：

  本文介绍了一种四组分一锅法连续合成α-Gal五糖2的方法，该方法在非常短的时间内即可实现最少的保护基操作。[结构：见文字]

  DOI：

  10.1021/ol0483246

文献信息

• A new one-pot synthesis of α-Gal epitope derivatives involved in the hyperacute rejection response in xenotransplantation
  作者：Yuhang Wang、Qingyan Yan、Jingping Wu、Li-He Zhang、Xin-Shan Ye

  DOI：10.1016/j.tet.2005.02.023

  日期：2005.4

  Xenotransplantations from pig to human are rapidly rejected because of the interaction between alpha-Gal epitopes carried by the graft and natural antibodies (anti-Gal antibodies) present in the blood of the recipient. This paper describes a three-component one-pot synthesis of three alpha-Gal related oligosaccharides with minimal protecting group manipulations in a very short period of time. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthetic Potential of Fucosyltransferase III for the Synthesis of Fluorescent‐labeled Milk Oligosaccharides
  作者：Said Rabbani、Federica Compostella、Laura Franchini、Beatrice Wagner、Luigi Panza、Beat Ernst

  DOI：10.1080/07328300500341965

  日期：2005.11.1

  Various fundamental biologic roles of milk oligosaccharides have been recognized; however, their structure-affinity relationship is still not fully revealed. Herein, we describe the synthesis of the fluorescent-labeled milk oligosaccharides 3-(5-dimethylaminonaphthalene-1-sulfonylamino)propyl beta-D-galactopyranosyl-(1 -> 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-2-acetamido-2-deoxy-beta-D-glucopyranoside (1) and 3-(5-dimethylamino-naphthalene-1-sulfonylamino)propyl beta-D-galactopyranosyl-(1 -> 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-beta-D-glucopyranoside (2) as useful tools for synthetic, analytic, and biologic applications. For the fucosylation of lactose and lacto- N -biose, the chemical and the enzymatic syntheses using fucosyltransferase III were compared.