ethyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-α-D-glucopyranoside | 1590421-92-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-α-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Mob(-4)]Glc(a)-SEt；[(2R,3R,4S,5R,6R)-6-ethylsulfanyl-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)oxan-2-yl]methanol
• CAS: 1590421-92-3
• 化学式: C₃₀H₃₆O₆S
• 分子量: 524.678
• InChiKey: MYWSMYHEHGMARS-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-α-D-glucopyranoside 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-4-O-(4-methoxybenzyl)-1-thio-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：

  ethyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-1-thio-α-D-glucopyranoside 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 以83%的产率得到ethyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-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

文献信息

• Rapid Synthesis of <scp>l</scp> -Idosyl Glycosyl Donors from α-Thioglucosides for the Preparation of Heparin Disaccharides
  作者：Mihály Herczeg、Fruzsina Demeter、Tímea Balogh、Viktor Kelemen、Anikó Borbás

  DOI：10.1002/ejoc.201800425

  日期：2018.7.6

  Synthesis of l‐idopyranosyl glycosyl donors starting from α‐ and β‐thio‐d‐glucopyranosides via the corresponding 5‐enopyranosides was studied for the first time. Hydroboration of the α‐configured 5‐enopyranosides proceeded with very high l‐ido stereoselectivity. After a 4,6‐O‐acetal formation, the obtained idosyl thioglycosides proved to be useful as donors in the synthesis of heparin‐related disaccharides

  的合成升-idopyranosyl糖基供体从α-和β硫代起始d -glucopyranosides经由相应的5- enopyranosides进行了研究，第一次。具有非常高的进行α-配置5- enopyranosides的硼氢化升- IDO立体选择性。在形成4,6- O-乙缩醛后，所获得的亚氨基磺酰糖苷被证明可作为肝素相关二糖合成的供体。
• Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity
  作者：Erika Mező、Mihály Herczeg、Dániel Eszenyi、Anikó Borbás

  DOI：10.1016/j.carres.2014.02.012

  日期：2014.3

  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.