ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside | 115234-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
• 英文别名: ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranose；[(2R,3S,4S,5R,6R)-5-azido-2-ethylsulfanyl-6-methyl-4-phenylmethoxyoxan-3-yl] acetate
• CAS: 115234-11-2
• 化学式: C₁₇H₂₃N₃O₄S
• 分子量: 365.453
• InChiKey: HOCMVXAAHBWIQA-VBCDNDGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside 在 sodium methylate 、 silver trifluoromethanesulfonate 、 三氟甲烷磺酸甲酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 methyl O-(2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  布鲁氏菌A和M抗原的抗原决定簇三，四和五糖的4,6-二脱氧-4-甲酰胺基-α-D-甘露糖的合成

  摘要：

  已经开发了基于使用硫代糖苷生成1,2-反式-糖苷键的合成策略，该策略已使五聚体α-1,2连接的4,6-二脱氧-4-甲酰胺基-α - D-甘露糖有效合成。均聚物以及包含α-1,3键的结构。

  DOI：

  10.1039/c39870001648
• 作为产物：
  描述：

  methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 生成 ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  KIHLBERG, JAN;EICHLER, EVA;BUNDLE, DAVID R., CARBOHYDR. RES., 211,(1991) N, C. 59-75

  摘要：

  DOI：

文献信息

• Studies toward a conjugate vaccine for anthrax. Synthesis and characterization of anthrose [4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-d-glucopyranose] and its methyl glycosides
  作者：Rina Saksena、Roberto Adamo、Pavol Kováč

  DOI：10.1016/j.carres.2005.04.010

  日期：2005.7

  group and reduce the azido function. Subsequent N-acylation of the formed amine 5 with 3-hydroxy-3-methylbutyric acid gave the target methyl alpha-glycoside 6. Synthesis of methyl beta-anthroside (22) comprised the same sequence of reactions, starting from the known methyl 4-azido-3-O-benzyl-4,6-dideoxy-beta-D-mannopyranoside (17), which was prepared from 1. In the synthesis of anthrose (16), 1-thio-beta-glucoside

  炭疽病（16）及其甲基α-（6）和β-糖苷（22）的第一化学合成中的关键步骤是分别从三氟甲磺酸10、2和18中的C-2颠倒C-2的构型。常见的中间体，甲基4-叠氮基-3-O-苄基-4,6-二脱氧-α-D-甘露吡喃糖苷（1）。为了制备甲基α-蒽苷（6），将从2中获得的葡萄糖产物3在O-2处甲基化，然后对所形成的2-甲基醚4进行氢化/氢解，以同时除去保护性苄基并还原叠氮功能。随后将形成的胺5用3-羟基-3-甲基丁酸进行N-酰化，得到目标甲基α-糖苷6。甲基β-蒽苷（22）的合成从已知的甲基4-开始，包括相同的反应顺序。叠氮基-3-O-苄基-4,6-二脱氧-β-D-甘露吡喃糖苷（17），
• Neoglycoconjugates from synthetic tetra- and hexasaccharides that mimic the terminus of the O-PS of Vibrio cholerae O:1, serotype Inaba
  作者：Xingquan Ma、Rina Saksena、Anatoly Chernyak、Pavol Kováč

  DOI：10.1039/b211660j

  日期：2003.2.27

  nic acid side chain already attached have been prepared and used for the synthesis of the di-through to the hexasaccharide that mimic the upsteam terminus of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Inaba. The target tetra- and the hexasaccharide, which were obtained in the form of 5-methoxycarbonylpentyl glycosides, were linked to BSA using squaric acid diester chemistry. The

  已经制备了具有已连接的N-3-脱氧-L-甘油-四氢电子酸侧链的糖基受体和糖基供体，并将其用于合成模仿O-的上游端的六糖的二通。霍乱弧菌O：1血清型Inaba的特定多糖。使用方酸二酯化学方法将以5-甲氧基羰基戊基糖苷形式获得的目标四糖和六糖与BSA连接。通过表面增强的激光解吸电离飞行时间质谱仪（SELDI-TOF MS）监测共轭反应。当达到所需的半抗原/ BSA摩尔比时，这可以控制合成寡糖的结合过程，并终止反应，产生具有预定碳水化合物/载体比的新糖缀合物。通过SELDI-TOF MS技术监测结合的能力，使得在一锅反应中从一个半抗原中制备出几种具有不同预定碳水化合物/载体比的新糖结合物成为可能。
• The synthesis of antibody binding-site probes: a hexasaccharide and two pentasaccharides related to the Brucella A antigen and prepared by in situ activation of thioglycosides with bromine
  作者：Jan Kihlberg、David R. Bundle

  DOI：10.1016/0008-6215(92)84151-h

  日期：1992.9

  glycosides. The pentasaccharide analogues each have two formamido groups replaced by hydroxyl groups. Protected derivatives of the three oligosaccharides were prepared by in situ activation with bromine of mono- and di-saccharide thioglycosides of D-rhamnose and 4-azido-4,6-dideoxy-D-mannose in the presence of a glycosyl acceptor and silver triflate as promoter. Reduction of the azido groups with hydrogen sulfide

  制备了两个五糖类似物和布鲁氏菌A抗原[---- 2]-α-D-Rhap4NFo-（1 ----] n的六糖片段作为甲基糖苷，每个五糖类似物具有两个甲酰胺基。三种寡糖的保护衍生物是通过在D-鼠李糖和4-azido-4,6-dideoxy-D-甘露糖存在下用D-鼠李糖和4-azido-4,6-dideoxy-D-甘露糖的单糖和二糖硫糖苷的溴原位活化来制备的。糖基受体和三氟甲磺酸银作为促进剂，用硫化氢还原叠氮基，用甲酸乙酯进行N-甲酰化，然后氢解，得到目标五糖苷。
• The design and synthesis of antibody binding site probes: three pentasaccharide analogues of the Brucella A antigen prepared by activation in situ of thioglycosides with bromine
  作者：Jan Kihlberg、Eva Eichler、David R. Bundle

  DOI：10.1016/0008-6215(91)84146-6

  日期：1991.4

  formamido group replaced by a hydroxyl group, have been prepared as their methyl glycosides. Mono- and di-saccharide thioglycosides of D-rhamnose and 4-azido-4,6-dideoxy-D-mannose were used as glycosyl donors for the preparation of protected pentasaccharide derivatives with trisaccharides as intermediates. Glycosylations were performed by activation in situ of the thioglycosides with bromine in the presence

  已制备了布鲁氏菌A抗原[---- 2）-alpha-D-Rhap4NFo-（1 ----）的三个五糖类似物，每个类似物均被一个甲基取代，并带有一个甲酰胺基。用D-鼠李糖和4-叠氮基-4,6-二脱氧-D-甘露糖的-和二糖硫糖苷作为糖基供体，以三糖为中间体制备受保护的五糖衍生物，通过原位活化糖基化来进行糖基化。在糖基受体和三氟甲磺酸银作为助催化剂存在下，用溴将硫代糖苷与溴化；用硫化氢还原叠氮基；用甲酸乙酯进行N-甲酰化，然后氢解得到目标五糖。
• Synthesis of spacer-equipped di-, tri-, and the tetrasaccharide fragments of the deacetylated O-PS1 of Citrobacter gillenii O9a,9b, and a related pentasaccharide
  作者：Rina Saksena、Anatoli Chernyak、Pavol Kováč

  DOI：10.1016/j.carres.2008.03.037

  日期：2008.7

  The title rhamnooligosaccharides [alpha-D-Rhap4NAc-(1 -> 3)-O(-D-Rhap4NAc-1-O-(CH2)(5)COOMe, alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-(1 3)-alpha-D-Rhap4NAc-1-O-(CH2)(5)COOMe, alpha-D-Rhap4NAc-(1 -> 2)-alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-1-O-(CH2)(5)COOMe, and alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-(1-2)-(alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc(1 -> 3)-alpha-D-Rhap4NAc-1-O-(CH2)(5)COOMe] were synthesized in a stepwise fashion from 5-methoxycarbonylpentyl 4-azido-4, 6-dideoxy-2-O-benzyl-alpha-D-mannopyranoside and orthogonally protected 1-thioglycoside glycosyl donors. The amorphous, final products were fully characterized as corresponding per-O-acetyl derivatives. Published by Elsevier Ltd.