N-phenyl-β-D-galactopyranosylamine | 131176-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-phenyl-β-D-galactopyranosylamine
• 英文别名: N-β-D-galactopyranosylaniline；D-Galactose-phenylimin；(d-Galaktose)-anil；(2R,3R,4S,5R,6R)-2-anilino-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 131176-28-8
• 化学式: C₁₂H₁₇NO₅
• 分子量: 255.271
• InChiKey: LKZGXPMJCWRGTC-YBXAARCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-phenyl-β-D-galactopyranosylamine 、 乙酸酐 在 吡啶 作用下， 生成 tetra-O-acetyl-N-phenyl-α-D-galactopyranosylamine
  参考文献：
  名称：

  Butler et al., Journal of the Chemical Society, 1949, p. 3371,3373

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3S,4S,5R,6R)‐2‐(acetoxymethyl)‐6‐(phenylamino)tetrahydro‐2H‐pyran‐3,4,5‐triyl triacetate 在 甲醇 、 sodium methylate 作用下， 生成 N-phenyl-β-D-galactopyranosylamine
  参考文献：
  名称：

  Butler et al., Journal of the Chemical Society, 1949, p. 3371,3373

  摘要：

  DOI：

文献信息

• Synthesis of bis(glycosylamino)alkanes and bis(glycosylamino)arenes
  作者：S. V. Metlitskikh、A. M. Koroteev、M. P. Koroteev、A. S. Shashkov、A. A. Korlyukov、M. Yu. Antipin、A. I. Stash、E. E. Nifantiev

  DOI：10.1007/s11172-006-0205-3

  日期：2005.12

  The condensation of D-mannose and D-galactose with aliphatic and aromatic diamines afforded a series of bis(glycosylamino)alkanes and-arenes. A possible mechanism was proposed for the formation of 1,2-bis(β-D-glycosylamino)benzenes.

  D-甘露糖和D-半乳糖与脂肪族和芳香族二胺缩合，生成了一系列双(糖基氨基)烷烃和双(糖基氨基)芳烃。对于1,2-双(β-D-糖基氨基)苯的形成，提出了一个可能的机制。
• One-pot stereoselective synthesis of β-N-aryl-glycosides by N-glycosylation of aromatic amines: application to the synthesis of tumor-associated carbohydrate antigen building blocks
  作者：Nicolas Bridiau、Moulay Benmansour、Marie Dominique Legoy、Thierry Maugard

  DOI：10.1016/j.tet.2007.02.092

  日期：2007.5

  We studied the stereoselective synthesis of several β-N-aryl-glycosides by glycosylation of aromatic primary amines using unprotected carbohydrates in aqueous solution. This was the first report showing an efficient method for the synthesis with one step of β-N-glycosyl-para-amino-phenyl alanine building blocks for the tumor-associated carbohydrate antigen (TACA) glycopeptides synthesis. Analysis of

  我们研究了在水溶液中使用未保护的碳水化合物通过芳香族伯胺的糖基化对几种β- N-芳基-糖苷进行的立体选择性合成。这是第一份报告，其显示了一种有效的合成方法，该方法可一步合成β- N-糖基-对氨基-苯丙氨酸，用于肿瘤相关的碳水化合物抗原（TACA）糖肽合成。通过1 H和13 C NMR对产物进行分析表明，在形成立体选择性β-N-糖苷键（天然N-糖蛋白键）之后，没有发生过Amadori重排。β- N在水介质中化学和酶稳定性的研究还研究了合成的-芳基-糖苷。首次我们显示，N-糖苷键在pH接近7时相对稳定，并且比O-糖苷键对酶水解更稳定。N-糖苷键的较高的酶和化学稳定性对于设想进一步开发稳定的TACA结构单元至关重要。
• Molecular and crystal structures of N-aryl-β-d-glycopyranosylamines from mannose and galactose
  作者：Charles R Ojala、Joanne M Ostman、Summer E Hanson、William H Ojala

  DOI：10.1016/s0008-6215(01)00117-3

  日期：2001.6

  The molecular and crystal structures of 12 N-aryl-beta -D-glycopyranosylamines have been determined by X-ray crystallography. Six of these are mannose derivatives, the N-p-bromophenyl (1), N-p-tolyl (2), N-m-chlorophenyl (3), N-p-methoxyphenyl (4), N-o-chloroyhenyl (5), and N-o-tolyl (6) derivatives that are formed by reaction with the corresponding substituted anilines. The remaining six are galactose derivatives, the N-phenyl (7), N-p-chlorophenyl (8), N-p-bromophenyl (9), N-p-iodophenyl (10), N-p-nitrophenyl (11) and N-p-tolyl (12), derivatives prepared similarly. Compounds 1 3 assume the same packing arrangement. Compounds 4, 5, and 6 assume unique packing an arrangements, although that assumed by 4 is closely related to that assumed by 1-3. Compounds 7-11 assume the same packing arrangement; that assumed by 12 is closely related to that assumed by 7-11. That the same packing arrangements can be maintained in spite of substantial changes in the electronic and steric nature of the substituent on the aryl ring reflects the strength of the hydrogen bond network connecting the monosaccharide portions of the molecules in the solid state. A hydrogen bonding motif found in all six mannose structures is a mutual interaction between translationally related molecules involving 0-3-(HO)-O-...-5 and O-6-(HO)-O-...-4 hydrogen bonds. The recurrence of this motif throughout this group of mannosylamines suggests that it is an especially favorable interaction that might be expected to occur also in related macromolecular systems. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Nanasi; Bognar, 1962, vol. 8, p. 49,53
  作者：Nanasi、Bognar

  DOI：——

  日期：——
• Nanasi; Bognar, Magyar Kemiai Folyoirat, 1962, vol. 68, p. 32,34
  作者：Nanasi、Bognar

  DOI：——

  日期：——