ethyl (2,3-di-O-methyl-α-D-glucopyranosyl)-(1->4)-2,3-di-O-methyl-1-thio-β-D-glucopyranoside | 202647-73-2

• 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-methyl-α-D-glucopyranosyl)-(1->4)-2,3-di-O-methyl-1-thio-β-D-glucopyranoside
• 英文别名: Glc2Me3Me(a1-4)Glc2Me3Me(b)-SEt；(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6S)-6-ethylsulfanyl-2-(hydroxymethyl)-4,5-dimethoxyoxan-3-yl]oxy-2-(hydroxymethyl)-4,5-dimethoxyoxan-3-ol
• CAS: 202647-73-2
• 化学式: C₁₈H₃₄O₁₀S
• 分子量: 442.528
• InChiKey: XJECGYCURIESBH-TXSAWVTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ethyl (2,3-di-O-methyl-α-D-glucopyranosyl)-(1->4)-2,3-di-O-methyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 反应 3.5h， 生成 ethyl (6-O-acetyl-4-O-levulinyl-2,3-di-O-methyl-α-D-glucopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-methyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic Carbohydrate Derivatives as Low Sulfated Heparin Mimetics

  摘要：

  The total synthesis of a new family of heparin mimetics containing an hexadeca- (2), an octadeca- (3), and an eicosasaccharide (4) is described. All three oligosaccharides contain a pentasaccharidic antithrombin binding domain(DEFGH: van Boeckel, C. A. A.; Petitou, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1671-1690), extended at the nonreducing end by a thrombin binding domain composed of repeated 2,3-di-O-methyl-6-O-sodium sulfonato-alpha-D-glucosyl units, The targets were synthesized using a key dodecasaccharide imidate as glycosyl donor as well as di- and tetrasaccharide imidates, all derived from maltose. Condensation of these imidates with a tetrasaccharide precursor of the EFGH part of the antithrombin binding domain gave fully protected hexadeca-, octadeca-, and eicosasaccharide that were deprotected and sulfated to yield 2, 3, and 4. All three displayed antithrombin-mediated antifactor Xa and antithrombin (factor IIa) activity. The most active compound, the eicosasaccharide, showed activity similar to that of low molecular weight heparin. Significantly, unlike heparin and its derivatives, the present: heparin mimetics do not interact with platelet factor 4, an interaction that can cause severe side effects in heparin-treated patients. Thus, this new family of compounds contains interesting drug candidates for the prevention and treatment of thrombosis.

  DOI：

  10.1021/jo991152j
• 作为产物：
  描述：

  ethyl (4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-6-O-trityl-1-thio-β-D-glucopyranoside 在 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 ethyl (2,3-di-O-methyl-α-D-glucopyranosyl)-(1->4)-2,3-di-O-methyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic Carbohydrate Derivatives as Low Sulfated Heparin Mimetics

  摘要：

  The total synthesis of a new family of heparin mimetics containing an hexadeca- (2), an octadeca- (3), and an eicosasaccharide (4) is described. All three oligosaccharides contain a pentasaccharidic antithrombin binding domain(DEFGH: van Boeckel, C. A. A.; Petitou, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1671-1690), extended at the nonreducing end by a thrombin binding domain composed of repeated 2,3-di-O-methyl-6-O-sodium sulfonato-alpha-D-glucosyl units, The targets were synthesized using a key dodecasaccharide imidate as glycosyl donor as well as di- and tetrasaccharide imidates, all derived from maltose. Condensation of these imidates with a tetrasaccharide precursor of the EFGH part of the antithrombin binding domain gave fully protected hexadeca-, octadeca-, and eicosasaccharide that were deprotected and sulfated to yield 2, 3, and 4. All three displayed antithrombin-mediated antifactor Xa and antithrombin (factor IIa) activity. The most active compound, the eicosasaccharide, showed activity similar to that of low molecular weight heparin. Significantly, unlike heparin and its derivatives, the present: heparin mimetics do not interact with platelet factor 4, an interaction that can cause severe side effects in heparin-treated patients. Thus, this new family of compounds contains interesting drug candidates for the prevention and treatment of thrombosis.

  DOI：

  10.1021/jo991152j

文献信息

• Synthetic Carbohydrate Derivatives as Low Sulfated Heparin Mimetics
  作者：Pierre-A. Driguez、Isidore Lederman、Jean-M. Strassel、Jean-M. Herbert、Maurice Petitou

  DOI：10.1021/jo991152j

  日期：1999.12.1

  The total synthesis of a new family of heparin mimetics containing an hexadeca- (2), an octadeca- (3), and an eicosasaccharide (4) is described. All three oligosaccharides contain a pentasaccharidic antithrombin binding domain(DEFGH: van Boeckel, C. A. A.; Petitou, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1671-1690), extended at the nonreducing end by a thrombin binding domain composed of repeated 2,3-di-O-methyl-6-O-sodium sulfonato-alpha-D-glucosyl units, The targets were synthesized using a key dodecasaccharide imidate as glycosyl donor as well as di- and tetrasaccharide imidates, all derived from maltose. Condensation of these imidates with a tetrasaccharide precursor of the EFGH part of the antithrombin binding domain gave fully protected hexadeca-, octadeca-, and eicosasaccharide that were deprotected and sulfated to yield 2, 3, and 4. All three displayed antithrombin-mediated antifactor Xa and antithrombin (factor IIa) activity. The most active compound, the eicosasaccharide, showed activity similar to that of low molecular weight heparin. Significantly, unlike heparin and its derivatives, the present: heparin mimetics do not interact with platelet factor 4, an interaction that can cause severe side effects in heparin-treated patients. Thus, this new family of compounds contains interesting drug candidates for the prevention and treatment of thrombosis.