2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-L-idopyranosyl trichloroacetimidate | 1591904-70-9

• 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: 2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-L-idopyranosyl trichloroacetimidate
• CAS: 1591904-70-9
• 化学式: C₁₈H₂₀Cl₃NO₇
• 分子量: 468.718
• InChiKey: YBQRJZHIJBVVRO-ZOWPNOISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  96.3
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-L-idopyranosyl trichloroacetimidate 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 33.33h， 生成 methyl [methyl (2-O-acetyl-3-O-methyl-α-l-idopyranosyl)uronate]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity

  摘要：

  Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl a-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.02.012
• 作为产物：
  描述：

  C₁₈H₂₂O₈ 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苄胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-L-idopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity

  摘要：

  Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl a-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.02.012

文献信息

• New synthesis of idraparinux, the non-glycosaminoglycan analogue of the antithrombin-binding domain of heparin
  作者：Mihály Herczeg、Erika Mező、Dániel Eszenyi、Sándor Antus、Anikó Borbás

  DOI：10.1016/j.tet.2014.03.033

  日期：2014.5

  heparin-related pentasaccharide possessing selective factor Xa inhibitory activity, was prepared by a new synthetic pathway. This route was based on a [2+3] block synthesis utilizing a 6-O-silyl-protected l-idose-containing trisaccharide acceptor, which was glycosylated with a disaccharide donor containing a non-oxidized precursor of the glucuronic acid. The unique strategy of multiple functionalizations

  通过新的合成途径制备了具有完全选择性的Xa抑制活性的完全O-硫酸化，O-甲基化，肝素相关的五糖Idraparinux 。该途径基于利用6 - O-甲硅烷基保护的含1 -ID糖的三糖受体的[2 + 3]嵌段合成，所述三糖受体被含有葡糖醛酸的非氧化前体的二糖供体糖基化。在五糖水平上进行多种功能化的独特策略，涉及三甲基化，然后将葡萄糖和同糖前体氧化为d-葡萄糖醛酸和l一步法证明β-异戊糖酸是高效的，通过从d-葡萄糖和甲基α- d-吡喃葡萄糖苷开始的39步合成来提供目标五糖。