3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl chloride | 67817-37-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl chloride
• 英文别名: 2-azido-β-D-galactosyl chloride；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-azido-6-chlorooxan-2-yl]methyl acetate
• CAS: 67817-37-2
• 化学式: C₁₂H₁₆ClN₃O₇
• 分子量: 349.728
• InChiKey: DOGAQWBZVNXURX-OZRWLHRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl chloride 在 molecular sieve 、 silver perchlorate 、 silver carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 78.0h， 生成 6-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  对于固相糖肽合成中的Fmoc裂解，哌啶比吗啉更可取，例如与HIV gp120和粘蛋白有关的糖肽的制备就是例证

  摘要：

  在Tn的抗原[将Fmoc-丝氨酸/苏氨酸（AC的被保护的衍生物3 GalNAcα）-OH，化合物5和8 ]已经制备通过将Fmoc-丝氨酸/苏氨酸- O-烯丙基糖基化与3,4,6-三- ø -乙酰基-2-叠氮基-2-脱氧-D-吡喃半乳糖基氯（2），然后将叠氮基转化为乙酰胺并脱脱甲酰。导数5和8用于固相合成与HIV gp120和粘蛋白有关的糖肽。在这些合成中，发现哌啶可有效去除Fmoc，而吗啉的脱保护作用缓慢且在某些步骤中不完全。与先前的关注相反，当哌啶用于Fmoc脱保护时，没有遇到糖肽立体中心的β-消除和差向异构化。然而，发现对于糖肽而言，其侧链脱保护并从固相切割。

  DOI：

  10.1016/0040-4020(96)00369-9
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl nitrate 在 四乙基氯化铵 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 9.5h， 生成 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl chloride
  参考文献：
  名称：

  Syntheses of TN building blocks Nα-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-galactopyranosyl)-l-serine/l-threonine pentafluorophenyl esters: comparison of protocols and elucidation of side reactions

  摘要：

  T-N antigen building blocks N-alpha-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl)-L-serine/L-threonine pentafluorophenyl ester [Fmoc-L-Ser/L-Thr(Ac-3-alpha-D-GalN(3))-OPfP, 13/14] have been synthesized by two different routes, which have been compared. Overall isolated yields [three or four chemical steps, and minimal intermediary purification steps] of enantiopure 13 and 14 were 5-18% and 6-10%, respectively, based on 3,4,6-tri-O-acetyl-D-galactal (1). A byproduct of the initial azidonitration reaction of the synthetic sequence, that is, N-acetyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosylamine (5), has been characterized by X-ray crystallography, and shown by H-1 NMR spectroscopy to form complexes with lithium bromide, lithium iodide, or sodium iodide in acetonitrile-d(3). Intermediates 3,4,6-tri-O-acetyl-2-azido2-deoxy-alpha-D-galactopyranosyl bromide (6) and 3,4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-galactopyranosyl chloride (7) were used to glycosylate N-alpha-(9-fluorenylmethoxycarbonyl)-L-serine/L-threonine pentafluorophenyl esters [Fmoc-L-Ser/L-Thr-OPfp, 11/12]. Previously undescribed low-level dehydration side reactions were observed at this stage; the unwanted byproducts were easily removed by column chromatography. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.02.029

文献信息

• Selectin Inhibitors, Composition, and Uses Related Thereto
  申请人：EMORY UNIVERSITY

  公开号：US20160108092A1

  公开（公告）日：2016-04-21

  This disclosure relates to selectin inhibitors, compositions, and methods related thereto. In certain embodiments, the disclosure relates to glycopeptides that contain one more modified amino acids conjugated to a saccharide or polysaccharide. In certain embodiments, the disclosure relates to uses of the glycopeptides as anti-inflammatory, anti-thrombotic, or anti-metastatic agents.

  本公开涉及选择性抑制剂、相关组合物和方法。在某些实施例中，本公开涉及含有一个或多个修饰氨基酸与糖或多糖结合的糖肽。在某些实施例中，本公开涉及将糖肽用作抗炎、抗血栓或抗转移剂。
• Allyl esters as carboxy protecting groups in the synthesis of O-glycopeptides
  作者：Sieglinde Friedrich-Bochnitschek、Herbert Waldmann、Horst Kunz

  DOI：10.1021/jo00265a007

  日期：1989.2
• US4195174A
  申请人：——

  公开号：US4195174A

  公开（公告）日：1980-03-25
• US4308376A
  申请人：——

  公开号：US4308376A

  公开（公告）日：1981-12-29
• US4362720A
  申请人：——

  公开号：US4362720A

  公开（公告）日：1982-12-07