methyl 4-amino-4-deoxy-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-amino-4-deoxy-α-D-glucopyranoside
• 英文别名: Methyl-4-amino-4-deoxy-α-D-glucopyranosid；(2S,3R,4S,5S,6S)-5-amino-6-(hydroxymethyl)-2-methoxyoxane-3,4-diol
• 化学式: C₇H₁₅NO₅
• 分子量: 193.2
• InChiKey: LMHVHMYRVUPVRG-ZFYZTMLRSA-N

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：

  methyl 4-amino-4-deoxy-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 40.0h， 生成 Methyl-4-deoxy-4-<<(1S)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexen-1-yl->amino>-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of some analogues of methyl dehydro-oligobiosaminide (acarviosin)

  摘要：

  DOI：

  10.1016/s0008-6215(00)90465-8
• 作为产物：
  描述：

  methyl 4-azido-4-deoxy-α-D-glucopyranoside 在 镍 氢气 作用下， 以 甲醇 为溶剂， 以57%的产率得到methyl 4-amino-4-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  抗生素低聚抑制剂的共同结构单元的合成

  摘要：

  甲基 N-[(1S)-(1,2,4/3,5,6)-2,3,4,6-四羟基-5-(羟甲基)环己基]-4-氨基-4,6-二脱氧- α-D-吡喃葡萄糖苷是抗生素低聚抑制素的常见结构单元，已被合成并表征为七乙酸酯。

  DOI：

  10.1246/cl.1982.1729
• 作为试剂：
  描述：

  乙酸酐 、 (1S,2R,3R,4R,6S)-2,3-dihydroxy-7-(2,4-dinitrophenyl)-4-hydroxymethyl-7-azabicyclo<4.1.0>heptane 在 吡啶 、 methyl 4-amino-4-deoxy-α-D-glucopyranoside 作用下， 生成 methyl 2,3,6-tri-O-acetyl-4-deoxy-4-<(1R)-(1,2/3,6)-4-acetoxymethyl-2,3-diacetoxy-6-(2,4-dinitrophenylamino)cyclohexylamino>-α-D-glucopyranoside 、 methyl 2,3,6-tri-O-acetyl-4-deoxy-4-<(1R)-(1,3,5/2,4)-5-acetoxymethyl-3,4-diacetoxy-2-(2,4-dinitrophenylamino)cyclohexylamino>-α-D-glucopyranoside 、 (1R,4S,5R,6R,7R)-5,6-diacetoxy-7-(2,4-dinitrophenylamino)-2-oxabicyclo<3.2.1>octane
  参考文献：
  名称：

  Ogawa, Seiichiro; Tsunoda, Hidetoshi, Liebigs Annalen der Chemie, 1993, # 7, p. 755 - 770

  摘要：

  DOI：

文献信息

• Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides
  作者：Ian Cumpstey

  DOI：10.1016/j.carres.2009.09.008

  日期：2009.11

  This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioether or amine bridges to carbohydrates or other carbasugars.

  这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。
• Quantifying the Electronic Effects of Carbohydrate Hydroxy Groups by Using Aminosugar Models
  作者：Christian M. Pedersen、Jacob Olsen、Azra B. Brka、Mikael Bols

  DOI：10.1002/chem.201100020

  日期：2011.6.14

  their pKa values determined by titration. These model compounds were chosen because they are the amino derivatives of the most common glycosyl acceptors. From this study it was possible to evaluate the electron density at each of the given positions in the carbohydrate and compare them. Some general trends were observed: The basicity of the amino groups decreases in the order 6‐NH2>3‐NH2>2‐NH2>4‐NH2

  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。
• Generalized Anomeric Effect in <i>gem</i>-Diamines: Stereoselective Synthesis of α-<i>N</i>-Linked Disaccharide Mimics
  作者：Elena M. Sánchez-Fernández、Rocío Rísquez-Cuadro、Matilde Aguilar-Moncayo、M. Isabel García-Moreno、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1021/ol901125n

  日期：2009.8.6

  The orbital (negative hyperconjugation) contribution to the generalized anomeric effect is highly increased in bicyclic gem-diamines with a pseudoamide-type endocyclic nitrogen atom, which has been exploited for the stereoselective synthesis of configurationally stable α-N-linked azadisaccharide heteroanalogues of the natural disaccharides maltose and isomaltose as aglycon-sensitive inhibitors of isomaltase

  在具有假酰胺型内环氮原子的双环宝石-二胺中，轨道（负超共轭）对广义异头作用的贡献大大增加，已被用于立体选择性合成天然构型稳定的α- N-连接的氮杂二糖杂类似物二糖麦芽糖和异麦芽糖作为糖异糖苷酶的糖苷配基敏感抑制剂。
• Synthesis and biological activities of methyl oligobiosaminide and some deoxy isomers thereof
  作者：Yasushi Shibata、Yasuhiro Kosuge、Seiichiro Ogawa

  DOI：10.1016/0008-6215(90)84091-8

  日期：1990.5

  Methyl oligobiosaminide (1) the core structure of oligostatin C, and five analogues, the 6-hydroxy-(2), 2-deoxy- (3), 2-deoxy-6-hydroxy- (4), 3-deoxy- (5), and 3-deoxy-6-hydroxy derivatives (6), were synthesized by coupling the protected pseudo-sugar epoxide 46 with suitable methyl 4-amino-4-deoxy-alpha-D-hexopyranoside derivatives. Compounds 3 and 6 showed notable inhibitory activity against alpha-D-glucosidase

  甲基oligobiosaminide（1）的核心结构是oligostatin C和5个类似物，即6-羟基-（2），2-脱氧-（3），2-脱氧-6-羟基-（4），3-脱氧-（ 5）和3-脱氧-6-羟基衍生物（6）是通过将保护的假糖环氧化物46与合适的甲基4-氨基-4-脱氧-α-D-己吡喃糖苷衍生物偶联而合成的。化合物3和6分别显示出对α-D-葡糖苷酶和α-D-甘露糖苷酶的显着抑制活性，而化合物1几乎没有活性。
• Sorbistin, a new aminoglycoside antibiotic complex of bacterial origin. III. Structure determination.
  作者：MASATAKA KONISHI、SACHIKO KAMATA、TAKASHI TSUNO、KEI-ICHI NUMATA、HIROSHI TSUKIURA、TAKAYUKI NAITO、HIROSHI KAWAGUCHI

  DOI：10.7164/antibiotics.29.1152

  日期：——

  The structures of sorbistins A1, A2, B, C and D have been determined including stereochemistry. Sorbistins A1, A2 and B are composed of a 4-acyl-amino-4-deoxy-D-glucose and 1, 4-diamino-1, 4-dideoxy-D-sorbitol, the latter compound being hitherto undescribed in literature. Sorbistins C and D have the same aglycone of 1, 4-diamino-1, 4-dideoxy-D-sorbitol, which is linked with D-glucose and 4-amino-4-deoxy-D-glucose, respectively, through a glycosidic bond.

  已经确定了sorbistins A1、A2、B、C和D的结构，包括立体化学。sorbistins A1、A2和B由4-酰氨基-4-脱氧-D-葡萄糖和1,4-二氨基-1,4-二脱氧-D-山梨醇组成，后者在文献中尚未描述。sorbistins C和D具有相同的苷元1,4-二氨基-1,4-二脱氧-D-山梨醇，分别通过糖苷键与D-葡萄糖和4-氨基-4-脱氧-D-葡萄糖相连。