benzyl 2-azido-2,4-dideoxy-4-fluoro-β-D-mannopyranoside | 643751-64-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-azido-2,4-dideoxy-4-fluoro-β-D-mannopyranoside
• 英文别名: benzyl 2-azido-2,4-dideoxy-4-fluoro-beta-D-mannopyranoside；(2R,3S,4R,5S,6R)-5-azido-3-fluoro-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-ol
• CAS: 643751-64-8
• 化学式: C₁₃H₁₆FN₃O₄
• 分子量: 297.286
• InChiKey: RAKGNBBBNGHEKV-NAWOPXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  73.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 2-azido-2,4-dideoxy-4-fluoro-β-D-mannopyranoside 、 乙酸酐 在 5-acetamido-3,5,7-trideoxy-7-fluoro-D-glycero-β-D 作用下， 以to obtain N-acetyl-4-deoxy-4-fluoro-D-mannosamine的产率得到2-acetamido-2,4-dideoxy-4-fluoro-D-mannopyranoside
  参考文献：
  名称：

  Process for preparing glycopeptides having asparagine-linked oligosaccharides, and the glycopeptides

  摘要：

  在肽链的所需位置上具有至少一个天冬氨酸连接寡糖的肽糖化物的制备方法为：(1)酯化树脂的羟基和氨基保护有脂溶性保护基(AGFPG)的氨基酸的羧基，(2)去除保护基以形成自由氨基，(3)酰胺化自由氨基和AGFPG的氨基酸的羧基，(4)去除保护基，(5)重复步骤(3)和(4)，(6)酰胺化AGFPG的天冬氨酸连接寡糖的天冬氨酸部分的自由氨基和羧基，(7)去除保护基，(8)酰胺化AGFPG的氨基酸的自由氨基和羧基，(9)重复步骤(7)和(8)，(10)去除保护基，(11)用酸切断树脂；通过将唾液酸或其衍生物转移至上述肽糖化物而获得的肽糖化物。

  公开号：

  US08063202B2
• 作为产物：
  描述：

  Benzyl 2-azido-2,4-dideoxy-4-fluoro-3,6-di-O-pivaloyl-β-D-mannopyranoside 、 sodium methylate 在 silica gel 、 乙酸乙酯 、 正己烷 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以giving Compound (23) (in an amount of 105.3 mg, 91.6%的产率得到benzyl 2-azido-2,4-dideoxy-4-fluoro-β-D-mannopyranoside
  参考文献：
  名称：

  Process for preparing glycopeptides having asparagine-linked oligosaccharides, and the glycopeptides

  摘要：

  在肽链的所需位置上具有至少一个天冬氨酸连接寡糖的肽糖化物的制备方法为：(1)酯化树脂的羟基和氨基保护有脂溶性保护基(AGFPG)的氨基酸的羧基，(2)去除保护基以形成自由氨基，(3)酰胺化自由氨基和AGFPG的氨基酸的羧基，(4)去除保护基，(5)重复步骤(3)和(4)，(6)酰胺化AGFPG的天冬氨酸连接寡糖的天冬氨酸部分的自由氨基和羧基，(7)去除保护基，(8)酰胺化AGFPG的氨基酸的自由氨基和羧基，(9)重复步骤(7)和(8)，(10)去除保护基，(11)用酸切断树脂；通过将唾液酸或其衍生物转移至上述肽糖化物而获得的肽糖化物。

  公开号：

  US08063202B2

文献信息

• Process for producing sugar peptide having asparagine sugar chain and the sugar peptide
  申请人：Kajihara Yasuhiro

  公开号：US20050222382A1

  公开（公告）日：2005-10-06

  Glycopeptide having at least one asparagine-linked oligosaccharide at a desired position of the peptide chain obtained by: (1) esterifying hydroxyl of a resin and carboxyl of an amino acid having amino group nitrogen protected with a fat-soluble protective group (AGFPG), (2) removing the protective group to form a free amino group, (3) amidating the free amino group and carboxyl of an amino acid having AGFPG, (4) removing the protective group, (5) repeating the steps (3) and (4), (6) amidating the free amino group and carboxyl of the asparagine portion of an asparagine-linked oligosaccharide having AGFPG, (7) removing the protective group, (8) amidating the free amino group and carboxyl of an amino acid having AGFPG, (9) repeating steps (7) and (8), (10) removing the protective group, and (11) cutting off the resin with an acid; glycopeptide obtained by transferring sialic acid or a derivative thereof to the above glycopeptide.

  具有至少一个天冬氨酸连接的寡糖在肽链的所需位置的糖肽的制备方法为：(1)酯化树脂的羟基和氨基保护有脂溶性保护基的氨基酸的羧基，(2)去除保护基以形成自由氨基，(3)酰胺化自由氨基和氨基酸的羧基，该氨基酸保护有脂溶性保护基，(4)去除保护基，(5)重复步骤(3)和(4)，(6)酰胺化天冬氨酸连接的寡糖的天冬氨酸部分和氨基酸的羧基，该氨基酸保护有脂溶性保护基，(7)去除保护基，(8)酰胺化自由氨基和氨基酸的羧基，该氨基酸保护有脂溶性保护基，(9)重复步骤(7)和(8)，(10)去除保护基，(11)用酸切断树脂;将唾液酸或其衍生物转移至上述糖肽获得的糖肽。
• PROCESS FOR PREPARING GLYCOPEPTIDES HAVING ASPARAGINE-LINKED OLIGOSACCHARIDES, AND THE GLYCOPEPTIDES
  申请人：Kajihara Yasuhiro

  公开号：US20120035345A1

  公开（公告）日：2012-02-09

  Glycopeptide having at least one asparagine-linked oligosaccharide at a desired position of the peptide chain obtained by: (1) esterifying hydroxyl of a resin and carboxyl of an amino acid having amino group nitrogen protected with a fat-soluble protective group (AGFPG), (2) removing the protective group to form a free amino group, (3) amidating the free amino group and carboxyl of an amino acid having AGFPG, (4) removing the protective group, (5) repeating the steps (3) and (4), (6) amidating the free amino group and carboxyl of the asparagine portion of an asparagine-linked oligosaccharide having AGFPG, (7) removing the protective group, (8) amidating the free amino group and carboxyl of an amino acid having AGFPG, (9) repeating steps (7) and (8), (10) removing the protective group, and (11) cutting off the resin with an acid; glycopeptide obtained by transferring sialic acid or a derivative thereof to the above glycopeptide.

  具有至少一个天冬氨酸连接寡糖在肽链的所需位置的糖肽，其制备方法为：（1）酯化树脂的羟基和具有脂溶性保护基（AGFPG）的氨基酸的羧基，其氨基团氮原子受保护；（2）去除保护基以形成自由氨基团；（3）酰胺化自由氨基团和具有AGFPG的氨基酸的羧基；（4）去除保护基；（5）重复步骤（3）和（4）；（6）酰胺化具有AGFPG的天冬氨酸连接寡糖的天冬氨酸部分的自由氨基团和羧基；（7）去除保护基；（8）酰胺化自由氨基团和具有AGFPG的氨基酸的羧基；（9）重复步骤（7）和（8）；（10）去除保护基；（11）用酸切割树脂；将唾液酸或其衍生物转移给上述糖肽获得的糖肽。
• PROCESS FOR PRODUCING SUGAR PEPTIDE HAVING ASPARAGINE SUGAR CHAIN AND THE SUGAR PEPTIDE
  申请人：OTSUKA CHEMICAL COMPANY, LTD.

  公开号：EP1520858A1

  公开（公告）日：2005-04-06

  A glycopeptide having at least one asparagine-linked oligosaccharide at a desired position of the peptide chain thereof, which is obtained by: (1) esterifying a hydroxyl group of a resin having the hydroxyl group and a carboxyl group of an amino acid having amino group nitrogen protected with a fat-soluble protective group, (2) removing the fat-soluble protective group to form a free amino group, (3) amidating the free amino group and a carboxyl group of an amino acid having amino group nitrogen protected with a fat-soluble protective group, (4) removing the fat-soluble protective group to form a free amino group, (5) repeating the steps (3) and (4) at least once, (6) amidating the free amino group and a carboxyl group of the asparagine portion of an asparagine-linked oligosaccharide having amino group nitrogen protected with a fat-soluble protective group, (7) removing the fat-soluble protective group to form a free amino group, (8) amidating the free amino group and a carboxyl group of an amino acid having amino group nitrogen protected with a fat-soluble protective group, (9) repeating the steps (7) and (8) at least once, (10) removing the fat-soluble protective group to form a free amino group, and (11) cutting off the resin with an acid; glycopeptide obtained by transferring sialic acid or a derivative thereof to the above glycopeptide using a sialic acid transferase.

  一种糖肽，在其肽链的一个所需位置上至少有一个天冬酰胺连接的寡糖，其获得方法是： (1) 将具有羟基的树脂的羟基和具有氨基氮的氨基酸的羧基用脂溶性保护基团酯化、 (2) 去除脂溶性保护基，形成游离氨基、 (3) 将游离氨基与具有氨基氮并被脂溶性保护基团保护的氨基酸的羧基酰胺化、 (4) 去除脂溶性保护基，形成游离氨基、 (5) 至少重复一次步骤(3)和(4) (6) 将游离氨基和天冬酰胺连接寡糖的天冬酰胺部分的羧基酰胺化，天冬酰胺连接寡糖的氨基氮被脂溶性保护基保护、 (7) 去除脂溶性保护基团以形成游离氨基、 (8) 将游离氨基与具有氨基氮并被脂溶性保护基团保护的氨基酸的羧基酰胺化、 (9) 至少重复一次步骤(7)和(8) (10) 去除脂溶性保护基，形成游离氨基，以及 (11)用酸切断树脂；利用硅氨酸转移酶将硅氨酸或其衍生物转移到上述糖肽中，得到糖肽。
• EP1520858B1
  申请人：——

  公开号：EP1520858B1

  公开（公告）日：2013-11-27
• US7943763B2
  申请人：——

  公开号：US7943763B2

  公开（公告）日：2011-05-17