6-chlorohexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 1220958-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 6-chlorohexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS: 1220958-03-1
• 化学式: C₂₁H₃₀ClNO₆
• 分子量: 427.925
• InChiKey: USLSGLPYCRHFRX-UCGFNCKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-chlorohexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 吡啶 、 三氟化硼乙醚 、 sodium cyanoborohydride 、 硫脲 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-3-O-[4,6-O-benzylidene-3-O-(chloroacetyl)-2-deoxy-2-(trichloroacetamido)-β-D-glucopyranosyl]-6-O-pivaloyl-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-3-O-[(2,2,2-trichloroethoxy)carbonyl]-β-D-glucopyranoside
  参考文献：
  名称：

  Aggregation of a Tetrasaccharide Acceptor Observed by NMR: Synthesis of Pentasaccharide Fragments of the Le^aLe^x Tumor-Associated Hexasaccharide Antigen

  摘要：

  We report the synthesis of a tetrasaccharide and two pentasaccharide fragments of the Le(a)Le(x) tumor-associated carbohydrate antigen alpha-L-Fuc-(1 -> 4)-[beta-d-Gal-(1 -> 3)]-beta-d-GlcNAc-(1 -> 3)-beta-d-Gal-(1 -> 4)-[alpha-l-Fuc-(1 -> 3)]-beta-d-GlcNAc-(1 -> OR). The choice of protecting groups permitted a one-step global deprotection (Na/NH3(l)). The protected chlorohexyl glycoside pentasaccharide was the precursor to the hexyl glycoside, to be used as a soluble inhibitor, and the aminohexyl glycoside analogue, to be conjugated to proteins for surface immobilization and immunization experiments. We observed that a linear tetrasaccharide that contained two N-acetylglucosamine residues and a free OH group gave two distinct sets of H-1 NMR signals when the data were acquired in deuterated chloroform. Data acquisition at variable concentrations and variable temperatures suggests that the second set of NMR signals results from aggregation of the tetrasaccharide driven by the formation of intermolecular H-bonds involving the NHAc. While the formation of intra- and intermolecular H-bonds involving N-acetylgucosamine residues has been reported in non-H-bonding solvents, this is, to our knowledge, the first time that these have lead to the appearance of two distinct sets of signals in the NMR spectra. This aggregation may explain the lack of reactivity observed when an attempt is made to glycosylate such an acceptor using non-H-bonding solvents such as dichloromethane.

  DOI：

  10.1021/acs.joc.5b00405
• 作为产物：
  描述：

  6-chlorohexyl 2-acetamido-2-deoxy-β-D-glucopyranoside 、 苯甲醛二甲缩醛 在 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以77%的产率得到6-chlorohexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Le 类似物的收敛合成。

  摘要：

  报道了从一种常见的受保护三糖合成三种 Le(x) 衍生物。这些类似物将分别用于竞争性结合实验、与载体蛋白的结合和在金上的固定。N-乙酰氨基葡萄糖单糖受体首先在 O-4 处用半乳糖基亚氨酸酯进行糖基化。这种耦合是在 40 摄氏度下进行的 BF(3).OEt(2) 过量激活，如果受体携带 6-氯己基而不是 6-叠氮己基苷元，则效果最好。然后将 6-氯己基二糖转化为受体并进行岩藻糖基化，产生相应的受保护的 6-氯己基 Le(x) 三糖。这种受保护的三糖被用作 6-叠氮己基的前体，6-乙酰硫代己基和 6-苄基硫代己基三糖类似物以极好的产率 (70-95%) 获得。反过来，我们描述了使用溶解金属条件在一个步骤中对这些中间体的脱保护。在这些条件下，6-氯己基和 6-叠氮己基中间体分别导致正己基和 6-氨基己基三糖目标。出乎意料的是，6-乙酰硫代己基类似物经过脱硫得到正己基糖苷产物，而6-苄基硫代己基类

  DOI：

  10.3762/bjoc.6.17

文献信息

• Synthesis of LacNAcLe^x- and DimLe^x-BSA Conjugates and Binding to Anti-Polymeric Le^xmAbs
  作者：Ali Nejatie、Sinthuja Jegatheeswaran、France-Isabelle Auzanneau

  DOI：10.1002/ejoc.201901142

  日期：2019.10.24

  The chemical synthesis of tetra‐ and pentasaccharide fragments of the tumor‐associated carbohydrate antigen dimeric Lewis X (dimLex) lacking either both or only the non‐reducing end fucosyl residues is described following a 1 + 1 + 1 synthetic strategy. Use of a 6‐chlorohexyl aglycon gave access to hexyl glycoside soluble inhibitors as well as the 6‐aminohexyl glycoside pentasaccharide. The 6‐aminohexyl glycoside pentasaccharide and a dimLex analogue were conjugated to BSA via a squarate linker and the glycoconjugates were shown by MALDI MS to both display an average of 16 oligosaccharides per BSA molecule. These glycoconjugates were used in the attempt to identify the smallest dimLex fragment required to maintain binding to mAbs SH2 and IG5F6, which are known to bind polymeric Lex structures preferentially over the monomeric Lex antigen. Titration studies showed that the non‐reducing end fucosyl residue in dimLex is involved in the recognition of the antigen by both mAbs SH2 and IG5F6.
• Anti-Lea monoclonal antibody SPM 522 recognizes an extended Lea epitope
  作者：Sinthuja Jegatheeswaran、Mickael Guillemineau、Richard Giovane、Louis Borrillo、Liang Liao、Deng Kuir、France-Isabelle Auzanneau

  DOI：10.1016/j.bmc.2022.116628

  日期：2022.2