2-azidoethyl 2,3,6-tri-O-phenylmethyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-phenylmethyl-β-D-glucopyranoside | 914772-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl 2,3,6-tri-O-phenylmethyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-phenylmethyl-β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-(2-azidoethoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 914772-38-6
• 化学式: C₅₆H₆₁N₃O₁₁
• 分子量: 952.114
• InChiKey: FRROMFKQNABSCY-NUGANNOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  70
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2,3,6-tri-O-phenylmethyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-phenylmethyl-β-D-glucopyranoside 、 在 4-甲基苯硫氯 、 silver trifluoromethanesulfonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以225.2 mg的产率得到2-azidoethyl (2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranosyl)-(1→4)-(2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl)-(1→4)-(2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1→4)-(2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranosyl)-(1→4)-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  一锅合成VII型B组链球菌多糖和二聚体的重复单元。

  摘要：

  VII型B组链球菌荚膜多糖的六糖重复单元的首次合成是通过单罐糖基化策略实现的。还通过一锅糖基化合成该重复单元的二聚体，以首先获得主链六糖，然后与侧链三糖供体一锅双糖基化。所有糖基化反应均具有出色的立体选择性，这利用了新的立体特异性α-糖基化方法和邻基团对1,2-反式糖基化的参与作用。

  DOI：

  10.1021/acs.orglett.9b00653
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 盐酸 、 IR resin (H+) 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 2-azidoethyl 2,3,6-tri-O-phenylmethyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-phenylmethyl-β-D-glucopyranoside
  参考文献：
  名称：

  An efficient glycosylation reaction for the synthesis of asialo GM2 analogues

  摘要：

  We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4'-OH of lactose derivatives (3a-d) to synthesize key intermediates of asialo GM2 analogues, and found that the glycosylation yield with 2a was 90% or more in all investigated cases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.008

文献信息

• Carbohydrate-lipid constructs and their use in preventing or treating viral infection
  申请人：Kode Biotech Limited

  公开号：US09226968B2

  公开（公告）日：2016-01-05

  The invention relates to selected carbohydrate-lipid constructs and their use as mimics of ligands for receptors expressed by virus. In particular, the invention relates to the use of selected carbohydrate-lipid constructs in methods of inhibiting virus infection and/or promoting clearance of virus from infected subjects. Carbohydrate-lipid constructs selected for use in these methods where the virus is Human Immunodeficiency Virus (HIV) are provided.

  这项发明涉及选定的碳水化合物-脂质构造物及其用作模拟病毒受体表达的配体的用途。具体地，该发明涉及选定的碳水化合物-脂质构造物在抑制病毒感染和/或促进感染主体中的病毒清除的方法中的应用。提供了用于这些方法中的选定碳水化合物-脂质构造物，其中病毒为人类免疫缺陷病毒（HIV）。
• Chemical synthesis of the tumor-associated globo H antigen
  作者：Satadru S. Mandal、Guochao Liao、Zhongwu Guo

  DOI：10.1039/c5ra00759c

  日期：——

  A derivative of the tumor-associated globo H antigen, a complex hexasaccharide, was synthesized by a convergent and efficient [3 + 2 + 1] strategy using various glycosylation methods. All glycosylation reactions afforded good to excellent yields and outstanding stereoselectivity, including the installation of cis α-linked D-galactose and L-fucose. The longest linear sequence for this synthesis was

  肿瘤相关的 globo H 抗原的衍生物，一种复杂的六糖，是使用各种糖基化方法通过收敛且有效的 [3 + 2 + 1] 策略合成的。所有糖基化反应均提供良好至优异的产率和出色的立体选择性，包​​括顺式α-连接的D-半乳糖和L-岩藻糖的安装。该合成的最长线性序列是半乳糖衍生物11的 11 个步骤，总产率为 2.6%。合成靶标在聚糖还原端具有游离的反应性氨基，有助于其与其他分子缀合以实现各种应用。
• Concise synthesis of sialic acid containing hexasaccharide corresponding to group B Streptococcus type IX capsular polysaccharide
  作者：Samim Sahaji、Tapasi Manna、Anup Kumar Misra

  DOI：10.1016/j.tet.2023.133499

  日期：2023.7

  has been developed for the synthesis of sialic acid containing hexasaccharide repeating unit having a 2-aminoethyl linker at the reducing end corresponding to the capsular polysaccharide of Group B Streptococcus type IX strain. A disaccharide thioglycoside has been prepared applying “orthogonal latent-active” glycosylation of a thioglycoside acceptor with a thioglycoside donor. A specially designed sialic

  已经开发了一种方便的块 [3 + 2+1] 糖基化策略，用于合成含有六糖重复单元的唾液酸，在还原端具有 2-氨基乙基接头，对应于 B 组链球菌IX 型菌株的荚膜多糖。应用硫糖苷受体与硫糖苷供体的“正交潜在活性”糖基化制备了二糖硫糖苷。一种特别设计的唾液酸硫糖苷供体已用于提供 α-糖苷键。在整个合成策略中，硫苷被用作糖基供体。N-碘代琥珀酰亚胺 (NIS) 和高氯酸的组合负载在二氧化硅上 (HClO 4 –SiO 2), 一种固体酸替代品, 被用作硫糖苷活化的亲硫促进剂。
• Synthesis of blood group Forssman pentasaccharide GalNAcα1-3GalNAcβ1-3Galα1-4Galβ1-4Glcβ–R
  作者：Inna S. Popova、Elena Yu. Korchagina、Marina A. Sablina、Alexander S. Paramonov、Annika K. Hult、Stephen M. Henry、Nicolai V. Bovin

  DOI：10.1016/j.mencom.2019.09.034

  日期：2019.9

  Synthesis of the glycan part of Forssman glycolipid GalNAc alpha 1-3GalNAc beta 1-3Gal alpha 1-4Gal beta 1-4Glc-Cer in the form of 2-aminoethyl glycoside has been carried out. The glycoside has been converted into a lipophilic derivative capable of controlled inserting into erythrocytes. The obtained surface-modified cells, termed kodecytes, revealed a high level of the blood group system FORS serological activity.
• An efficient glycosylation reaction for the synthesis of asialo GM2 analogues
  作者：Bin Sun、Aliaksei V. Pukin、Gerben M. Visser、Han Zuilhof

  DOI：10.1016/j.tetlet.2006.08.008

  日期：2006.10

  We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4'-OH of lactose derivatives (3a-d) to synthesize key intermediates of asialo GM2 analogues, and found that the glycosylation yield with 2a was 90% or more in all investigated cases. (c) 2006 Elsevier Ltd. All rights reserved.