methyl 2-amino-2-deoxy-α-D-mannopyranoside | 50991-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-amino-2-deoxy-α-D-mannopyranoside
• 英文别名: methyl α-D-mannosamine；Methyl-2-amino-2-deoxy-α-D-mannopyranosid；Methyl-2-amino-2-deoxy-alpha-D-mannopyranoside；(2R,3S,4R,5S,6S)-5-amino-2-(hydroxymethyl)-6-methoxyoxane-3,4-diol
• CAS: 50991-93-0
• 化学式: C₇H₁₅NO₅
• 分子量: 193.2
• InChiKey: UCMLSEINWYQAES-BIVRFLNRSA-N

物化性质

• 沸点：
  387.6±42.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 methyl 2-amino-2-deoxy-α-D-mannopyranoside 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 Methyl 2-deoxy-2-(N,N-dimethylamino)-α-D-mannopyranoside
  参考文献：
  名称：

  2-氨基糖的对苯基苄基醚和对苯基苯甲酸酯在cd幅度上的加性

  摘要：

  分开的CD曲线的幅度（A值）的加和关系对于氨基糖的对苯基苄基醚1-12和苯基苯甲酸酯13-28成立。因此，基于CD幅度的糖苷键确定方法也适用于含有氨基糖的寡糖。

  DOI：

  10.1016/s0040-4020(01)87751-6
• 作为产物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside 在 甲醇 、 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 methyl 2-amino-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  使用氨基糖模型量化碳水化合物羟基的电子效应

  摘要：

  合成了具有α-和β-葡萄糖，α-半乳糖或α-甘露糖立体化学的甲基氨基脱氧糖苷，在四个可能的非异头位置中均具有氨基官能团，并通过滴定确定了其p K a值。选择这些模型化合物是因为它们是最常见的糖基受体的氨基衍生物。通过这项研究，有可能评估碳水化合物中每个给定位置的电子密度并进行比较。观察到一些一般趋势：氨基的碱度以6-NH 2 > 3-NH 2 > 2-NH 2 > 4-NH 2的顺序降低。（指的是位置）。当糖环上的一个或多个取代基为轴向时，氨基脱氧糖α的碱性通常会增加。当胺对氧原子为反平面时，碱度降低。这些发现与从糖基化化学和糖的区域选择性保护获得的观察结果一致。

  DOI：

  10.1002/chem.201100020

文献信息

• Glucosamine derivative, process for preparing the same and synthetic intermediate thereof
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0653434A1

  公开（公告）日：1995-05-17

  There are disclosed a D-glucosamine derivative represented by the formula (I): wherein (1) X is a group of formula: and R¹ and R² are both hydrogen atoms; or (2) X is OH or a group of the formula:    and one of R¹ and R² is a group of the formula: -Y-R¹¹ or alkyl and the other is H, or one of R¹ and R² is a group of the formula: -Y-R¹¹ and the other is alkyl; Y is a group of the formula: -CO-, -CS- or -SO₂-; R¹¹ is alkyl, lower alkoxy, alkenyl, alkynyl, phenyl, cycloalkyl, tricycloalkyl, heterocyclic or alkylamino; R³ is H, phenyl, phenoxy, phenylthio, phenylamino or heterocyclic; R⁴ is alkanoyl, alkenoyl or alkynoyl; and Alk is alkylene, provided that a compound in which X is OH, one of R¹ and R² is methyl and the other is acetyl is excluded, or a pharmaceutically acceptable salt thereof, a process for preparing the same, and a synthetic intermediate thereof.

  公开了一种由式(I)表示的D-葡萄糖胺衍生物，其中(1)X是式的一个基团：而R¹和R²都是氢原子；或(2)X是OH或式的一个基团：和R¹和R²中的一个是式的基团：-Y-R¹¹或烷基，另一个是氢，或R¹和R²中的一个是式的基团：-Y-R¹¹，另一个是烷基；Y是式的基团：-CO-，-CS-或-SO₂-；R¹¹是烷基，低级烷氧基，烯基，炔基，苯基，环烷基，三环烷基，杂环或烷基氨基；R³是氢，苯基，苯氧基，苯硫基，苯胺基或杂环；R⁴是脂肪酰基，烯酰基或炔酰基；而Alk是烷基，但当X是OH，R¹和R²中的一个是甲基，另一个是乙酰基的化合物被排除，或其药学上可接受的盐，以及其制备方法和合成中间体。
• SYNTHETIC LIPOAMINO ACID GLUCOSAMINE DERIVATIVES FOR IMPROVEMENT OF PLANT GROWTH AND YIELD
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：US20160021879A1

  公开（公告）日：2016-01-28

  The invention provides compounds, formulations and methods for improving plant emergence, growth and yield. More specifically, the present invention relates to compositions comprising the synthetic lipoamino acid glucosamine compounds of Formula I. These compounds may be applied to plant propagating materials, including seeds and other regenerable plant parts, including cuttings, bulbs, rhizomes and tubers. They may also be applied to foliage, or soil either prior to or following planting of plant propagating materials. Such applications may be made alone or in combination with fungicides, insecticides, nematicides and other agricultural agents used to improve plant growth and crop yield. The compounds of Formula I can improve the agronomic performance of a variety of crops including barley, canola, corn, potato, soybean and wheat.

  本发明提供了用于改善植物出苗、生长和产量的化合物、配方和方法。更具体地说，本发明涉及包含化学合成的脂肽氨基糖化合物（公式I）的组合物。这些化合物可以应用于植物繁殖材料，包括种子和其他可再生植物部分，包括插条、鳞茎、根茎和块茎。它们也可以应用于叶片或土壤，无论是在种植植物繁殖材料之前还是之后。这种应用可以单独进行，也可以与杀菌剂、杀虫剂、线虫灭生剂和其他用于改善植物生长和作物产量的农业剂一起使用。公式I的化合物可以改善各种作物的农艺性能，包括大麦、油菜、玉米、马铃薯、大豆和小麦。
• Process for the preparation of cyclopropane carboxylic acid esters
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0022608A1

  公开（公告）日：1981-01-21

  3-Halogenoethyl- or propyl-2,2-dimethylcyclopropane carboxylic acid esters, which are intermediates in the preparation of synthetic pyrethroids, are prepared by the reaction of certain halogenopentenes or hexenes with a diazoacetic ester in the presence of a catalyst which is metallic copper or a copper (II) salt, a rhodium (II) salt of a carboxylic acid or a transition metal complex of certain chiral Schiff bases. By the use of the latter class of catalysts the yield of preferred cis IR isomer may be increased relative to the other possible isomers.

  3-卤代乙基-或丙基-2,2-二甲基环丙烷羧酸酯是制备合成拟除虫菊酯的中间体，其制备方法是某些卤代戊烯或己烯与重氮乙酸酯在金属铜或铜（II）盐、羧酸铑（II）盐或某些手性席夫碱的过渡金属络合物催化剂存在下进行反应。与其他可能的异构体相比，使用后一类催化剂可以提高优选顺式红外异构体的产率。
• Chiral sugar complexes and process for their preparation
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0024797A1

  公开（公告）日：1981-03-11

  Chiral Schiff bases according to the general formula: and chiral transition metal complexes thereof, wherein at least the carbon atom of the monosaccharide to which the iminyl nitrogen atom is attached is asymmetric, and at least one of the carbon atoms adjacent the aforesaid carbon atom bears a hydroxyl group, R1 and R6 which may be the same or different, are hydrogen or lower alkyl, R2 is hydrogen, or lower alkyl or together with R10 forms a divalent hydrocarbon group, R3 is hydrogen, a sugar residue, or-CH2OR10 in which R10 is hydrogen, lower alkyl or together with R2 forms a divalent hydrocarbon group, R4 is hydrogen or-CH2OR10 in which R10 is hydrogen, or a lower alkyl, R5 is hydrogen, OR1 or a sugar residue, provided that both R4 and R5 are not hydrogen, R7 and R8 which may be the same or different, are hydrogen, or lower alkyl, or where p is 1, may with the cyclic ring to which CR7R8 is attached form a fused system, R8 is hydrogen, alkyl, aralkyl, aryl or alkaryl, J is a chain of 3 or 4 atoms which with the group CK forms an aromatic system, which atoms may be carbon atoms or may be a mixture of carbon and one or more hetero atoms which may be the same or different, K is nitrogen, or =COH, =→O or -NH-, L each of which may be the same or different, represents a substituent attached to a carbon atom in the chain J and is hydrogen, an alkyl group, aralkyl group, aryl, alkaryl or a substituent containing a hetero-atom; or two L's together with cyclic group to which they are attached form a fused system, m is 0 or 1, n is 0,1 or 2, provided that n plus m is 0, 1, 2 or 3, p is 0, 1 or 2 and q is the number of carbon atoms in the chain J. Thetransition metal is for example copper (II), chromium (II), manganese (II), iron (II), cobalt (II), nickel (II) or palladium (II). The aforesaid complexes may be used as catalysts in the cyclopropanation of olefins by diazoacetates to form insecticide or insecticide precursors.

  根据通式的手性希夫碱： 及其手性过渡金属配合物，其中亚氨基氮原子所连接的单糖的至少一个碳原子是不对称的，与上述碳原子相邻的至少一个碳原子带有羟基，R1和R6可以相同或不同，是氢或低级烷基，R2是氢、R3 是氢、糖残基或-CH2OR10，其中 R10 是氢、低级烷基或与 R2 一起形成二价烃基；R4 是氢或-CH2OR10，其中 R10 是氢或低级烷基；R5 是氢、OR1 或糖残基，但 R4 和 R5 都不是氢、R7 和 R8 可以相同或不同，它们是氢、或低级烷基，或当 p 为 1 时，可与 CR7R8 所连接的环形成一个融合系统，R8 是氢、烷基、芳基、芳烷基或烷芳基，J 是 3 或 4 个原子的链，与基团 CK 形成一个芳香系统、其中的原子可以是碳原子，也可以是碳原子和一个或多个杂原子的混合物，杂原子可以是相同的，也可以是不同的；K 是氮，或 =COH、=→O 或 -NH-；L 每个可以是相同的，也可以是不同的，代表连接到链 J 中一个碳原子上的取代基，是氢、烷基、芳基、芳烷基或含有杂原子的取代基；或两个 L 与所连接的环状基团一起形成一个融合体系，m 为 0 或 1，n 为 0、1 或 2，条件是 n 加 m 为 0、1、2 或 3，p 为 0、1 或 2，q 为链 J 中的碳原子数。过渡金属例如为铜（II）、铬（II）、锰（II）、铁（II）、钴（II）、镍（II）或钯（II）。上述配合物可用作重氮乙酸酯环丙烷化烯烃的催化剂，以形成杀虫剂或杀虫剂前体。
• Novel nitrosourea derivative, process for preparing same and therapeutic composition containing said derivate
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：EP0062329A1

  公开（公告）日：1982-10-13

  A nitrosourea compound of the formula: wherein R1 is lower alkyl and R2 is lower alkyl or lower alkoxy-lower alkyl, which may be prepared by nitrosation of a compound of the formula: wherein R1 and R2 are the same as defined above. Said nitrosourea compound is useful as an anti-tumor or anti-leukemic agent.

  式中 R1 为低级烷基，R2 为低级烷基或低级烷氧基-低级烷基的亚硝基脲化合物，可通过对式中 R1 和 R2 与上述定义相同的化合物进行亚硝基化反应制备。 上述亚硝基脲化合物可用作抗肿瘤或抗白血病药物。