N-benzyl-D-glucopyranosylamine | 70428-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-D-glucopyranosylamine
• 英文别名: N-benzyl-β-D-glucopyranosylamine；N-Benzyl-β-D-glucopyranosylamin；N-Benzyl-β-D-glucopyranosylamine；N-Benzyl-ss-glucosylamin；(2R,3R,4S,5S,6R)-2-(benzylamino)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 70428-25-0
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: JMAHBQWKTCJRGQ-UJPOAAIJSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  497.2±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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-benzyl-D-glucopyranosylamine 以 乙醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis and fungicidal activity of alkaloid-containing carbohydrates

  摘要：

  N-Glycosylamines, triethylammonium salt of xylosyl- and glucosylbenzyldithiocarbamates, and their derivatives containing fragments of alkaloids were synthesized; some of these substances exhibit fungicidal activity.

  DOI：

  10.1134/s1070427206030402
• 作为产物：
  描述：

  苯甲醛 在 甲醇 、 氨 、 镍 、 乙酸乙酯 作用下， 生成 N-benzyl-D-glucopyranosylamine
  参考文献：
  名称：

  Helferich; Mitrowski, Chemische Berichte, 1952, vol. 85, p. 1,7

  摘要：

  DOI：

文献信息

• N-glycosylated carboxamide derivatives as growth-promoters in livestock
  申请人：Bayer Aktiengesellschaft

  公开号：US04680287A1

  公开（公告）日：1987-07-14

  Growth of animals is promoted by inclusion in their feed of compounds of the formula ##STR1## in which Z is a glycosyl radical bonded via the anomeric carbon atom, R.sub.1 is hydrogen or an optionally substituted hydrocarbon radical having up to 30 Carbon atoms optionally interrupted by O, N or S, and R.sub.2 is hydrogen or an alkyl or aralkyl radical having up to 30 Carbon atoms optionally interrupted by O or substituted by groups containing oxygen or by halogen, with the proviso that COR.sub.1 is not an acyl group having 1-5 Carbon atoms when R.sub.2 is an alkyl group having 10-20 Carbon atoms.

  动物生长可以通过在其饲料中添加以下化合物的形式得到促进：其中Z是通过异头碳原子连接的糖基自由基，R1是氢或者是一个最多含有30个碳原子，可以选择性地被O、N或S原子隔断的，也可以选择性地被取代的烃基团，而R2是氢或者是一个最多含有30个碳原子的烷基或芳烷基团，可以选择性地被O原子隔断或被含氧基团或卤素取代，条件是当R2是一个含有10-20个碳原子的烷基团时，COR1不能是一个含有1-5个碳原子的酰基团。
• N-glycosylated carboxamide derivatives and their use for influencing the
  申请人：Bayer Aktiengesellschaft

  公开号：US04683222A1

  公开（公告）日：1987-07-28

  The invention relates to N-glycosylated carboxamide derivatives of Formula I which are useful for influencing the body's inherent defenses, e.g. for increasing immune system antibodies. Also included in the invention are compositions containing said N-glycosylated carboxamide derivative of Formula I as active ingredients and methods for the use of said compounds and compositions.

  本发明涉及式I的N-糖基化羧酰胺衍生物，它们可用于影响机体的固有防御，例如用于增加免疫系统的抗体。发明还包括含有式I的N-糖基化羧酰胺衍生物作为活性成分的组合物，以及使用所述化合物和组合物的方法。
• N-glycosylated carboxylic acid derivatives as agents for combating
  申请人：Troponwerke GmbH & Co., KG

  公开号：US04710491A1

  公开（公告）日：1987-12-01

  A method of combating rheumatic diseases which comprises administering to a patient afflicted therewith an amount effective to combat such disease of a compound of the formula ##STR1## in which Z is a glycosyl radical bonded via the anomeric carbon atom, R.sub.1 is hydrogen or an optionally substituted hydrocarbon radical with up to 30 C atoms, which hydrocarbon radical is optionally interrupted by O, N or S, and R.sub.2 is hydrogen or an alkyl or aralkyl radical with up to 30 C atoms, which is optionally interrupted by O, N or S or substituted by an oxygen-containing group or halogen, with the proviso that COR.sub.1 is not an acyl group with 1-5 C atoms if R.sub.2 is alkyl with 10-20 C atoms.

  一种治疗风湿病的方法，包括给患者施用有效治疗该疾病的量的以下化合物的公式：##STR1## 其中Z是通过异构碳原子连接的糖基自由基，R1是氢或最多有30个碳原子的可选取代的烃基，该烃基可被O、N或S隔断，R2是氢或最多有30个碳原子的烷基或芳烷基，该基团可被O、N或S隔断或被含氧基团或卤素取代，条件是如果R2是10-20个碳原子的烷基，则COR1不是1-5个碳原子的酰基。
• Green glycosylation using ionic liquid to prepare alkyl glycosides for studying carbohydrate–protein interactions by SPR
  作者：F. Javier Muñoz、Sabine André、Hans-Joachin Gabius、José V. Sinisterra、María J. Hernáiz、Robert J. Linhardt

  DOI：10.1039/b814171a

  日期：——

  Several simple glycosides of D-glucose (Glc) and N-acetyl-D-galactosamine (GalNAc) were prepared in a single step glycosylation reaction using unprotected and unactivated sugar donors. The resulting GalNAc glycoside, containing a bifunctional linker, was used to immobilize this glycoconjugate to a self assembled monolayer on a gold biosensor chip. Surface plasmon resonance (SPR) experiments demonstrated that this immobilized glycoconjugate bound to GalNAc specific lectin, Viscum album agglutinin.

  通过使用未保护和未活化的糖供体，在一步糖基化反应中制备了几种简单的D-葡萄糖（Glc）和N-乙酰-D-半乳糖胺（GalNAc）的糖苷。得到的含有双功能连接子的GalNAc糖苷，被用来将这种糖缀合物固定在黄金生物传感器芯片上的自组装单层上。表面等离子体共振（SPR）实验证明，这种固定的糖缀合物能够与GalNAc特异性凝集素，即槲寄生凝集素结合。
• Direct Synthesis of β-<i>N</i>-Glycosides by the Reductive Glycosylation of Azides with Protected and Native Carbohydrate Donors
  作者：Jianbin Zheng、Kaveri Balan Urkalan、Seth B. Herzon

  DOI：10.1002/anie.201301264

  日期：2013.6.3

  A simple and straightforward method for the stereocontrolled synthesis of β‐linked N‐glycosides uses alkyl and aryl azides as the nitrogen source. The N‐glycosides are formed in high yields and with high β selectivities (typically >70 % yield, >15:1 β:α selectivity). This approach is also amenable to the synthesis of N‐glycosylated amino acids and peptides (see example, Fmoc=9‐fluorenylmethoxycarbonyl)

  一种简单直接的立体控制合成β-连接N-糖苷的方法，使用烷基和芳基叠氮化物作为氮源。N-糖苷的形成具有高产率和高 β 选择性（通常 >70% 产率，>15:1 β:α 选择性）。这种方法也适用于N-糖基化氨基酸和肽的合成（参见示例，Fmoc=9-芴基甲氧基羰基）。