methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-α-D-glucopyranoside | 74593-34-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-α-D-glucopyranoside
• 英文别名: Methyl-(4-azido-2,3,6-tri-O-benzoyl-4-desoxy-α-D-glucopyranosid)；methyl 4-azido-4-deoxy-2,3,6-tri-O-benzoyl-α-D-glucopyranoside；diazonio-[(2S,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-methoxyoxan-3-yl]azanide
• CAS: 74593-34-3
• 化学式: C₂₈H₂₅N₃O₈
• 分子量: 531.522
• InChiKey: KOYRPVHKPCBLIV-NRUNVSGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  146.12
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-α-D-glucopyranoside 在 吡啶 、 甲醇 、 2,2,6,6-四甲基哌啶氧化物 、 tin(II) chloride dihdyrate 、 硫酸 、 sodium methylate 、 三乙胺 、 4-甲苯硫酚 作用下， 以 甲醇 、 氯仿 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 171.17h， 生成
  参考文献：
  名称：

  一种新奥霉素的全合成方法

  摘要：

  本发明属于药物化学和有机合成技术领域，目的是提供一种化学全合成新奥霉素的方法，具体包括：以D‑半乳糖等为原料，首先通过8步反应得到化合物14，随后与尿嘧啶缩合得到化合物15，再通过4步反应得到化合物19，接着与化合物6进行缩合得到化合物20，最后依次脱除酯保护基，再脱除Cbz保护基得到天然产物新奥霉素。本发明是首次合成天然产物新奥霉素的方法。本发明具有产物纯度高、成本低和操作简单等优点。

  公开号：

  CN107973830B
• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 在 吡啶 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-α-D-glucopyranoside
  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

• Sensitive and specific enzyme immunoassays for antigenic trisaccharide from Bacillus anthracis spores
  作者：Sandrine G. Y. Dhénin、Vincent Moreau、Marie-Claire Nevers、Christophe Créminon、Florence Djedaïni-Pilard

  DOI：10.1039/b914534f

  日期：——

  A straightforward synthesis of an anthrose-containing trisaccharide derived from Bacillus anthracis was achieved. Antibodies raised against this hapten provide a highly sensitive enzyme immunoassay with a detection limit of 8.5 pmol mL−1. By investigating the specificity of the antibodies obtained using different mono-, di- and trisaccharide synthetic analogues, we demonstrated that the epitope was mainly made up of the methyl group at C-5, the butamido group at C-4 and the hydroxyl at C-3 of the anthrose unit, the other parts of the trisaccharide appearing little involved in the recognition.

  成功实现了一种来源于炭疽杆菌的含炭疽糖的三糖的直接合成。针对这种半抗原产生的抗体提供了高度敏感的酶免疫测定法，其检测限为8.5 pmol mL−1。通过研究使用不同单糖、二糖和三糖合成类似物获得的抗体的特异性，我们证明表位主要由炭疽糖单元中的C-5甲基、C-4丁酰胺基和C-3羟基组成，三糖的其他部分在识别中涉及较少。
• Glucose Positions Affect the Phloem Mobility of Glucose–Fipronil Conjugates
  作者：Zhiwei Lei、Jie Wang、Genlin Mao、Yingjie Wen、Yuxin Tian、Huawei Wu、Yufeng Li、Hanhong Xu

  DOI：10.1021/jf5010429

  日期：2014.7.2

  In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.
• Synthesis of 4-deoxy-d-xylo-hexose and 4-azido-4-deoxy-d-glucose and their effects on lactose synthase
  作者：Sudhir K. Sinha、Keith Brew

  DOI：10.1016/s0008-6215(00)85655-4

  日期：1980.5

  Syntheses are reported of 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose as potential inhibitors for lactose synthase [uridine 5'-(alpha-D-galactopyranosyl pyrophosphate):D-glucose 4-beta-D-galactopyranosyltransferase, EC 2.4.1.22]. These syntheses involved SN2 displacement of the 4-methylsulfonyloxy group of methyl 2,3,6-tri-O-benzoyl-4-O-methylsulfonyl-alpha-D-galactopyranoside by iodide and azide ions. In both cases, inversion in configuration was observed. The resulting intermediates, methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-alpha-D-glucopyranoside and methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-alpha-D-glucopyranoside, were obtained in crystalline form. Both 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose were found to be inhibitors for lactose synthase in the presence of alpha-lactalbumin, but had no effect in the absence of alpha-lactalbumin. Both D-glucose analogues bind to the enzyme system far more weakly than D-glucose, suggesting that the recognition of the 4-OH group of the acceptor substrate is an important factor in binding.
• SACCHAROPEPTIDES AND DERIVATIVES THEREOF
  申请人：GLYCOMED INCORPORATED

  公开号：EP0824538A1

  公开（公告）日：1998-02-25
• [EN] SACCHAROPEPTIDES AND DERIVATIVES THEREOF<br/>[FR] SACCHAROPEPTIDES ET DERIVES
  申请人：——

  公开号：WO1996035700A1

  公开（公告）日：1996-11-14

  [EN] The present invention describes glycomimetic saccharopeptides of formula (I): W-(X)n-Y-[(X)n-W-(X)n-Y]m-(X)n-W, wherein W is independently selected from the group consisting of a) saccharides; b) aryl, aralkyl; c) alkyl of 1 to 8 carbon atoms, optionally substituted; d) cyclic alkyl or 5-7 carbon atoms, heterocyclic alkyl. Y is independently selected from the group consisting of -NR<3>-C(O)- and -C(O)-NR<3>-; X is a difunctional or polyfunctional group selected from the group consisting of a) aryl, aralkyl; b) alkyl of 1-8 carbon atoms, optionally substituted with 1-3 substituents. R is -H, or lower alkyl, lower aryl, and lower aralkyl; R' is independently selected from the group consisting of -H, lower alkyl of 1-4 carbon atoms, aralkyl of 2 to 19 carbon atoms, and -C(O)R"; R" is lower alkyl of 1 to 4 carbon atoms; and R<3> is selected from the group consisting of -H, alkyl of 1-8 carbon atoms, and aralkyl of 5-8 carbon atoms; and pharmaceutically acceptable salts thereof.
  [FR] La présente invention concerne des saccharopeptides glycomimétiques représentés par la formule générale (I): W-(X)n-Y-[(X)n-W-(X)n-Y]m-(X)n-W ainsi que certains de ses sels pharmacologiquement admis. Dans cette formule, W est choisi indépendamment dans le groupe constitué a) des saccharides, b) des aryles et aralkyles, c) des alkyles portant 1 à 8 atomes de carbone, éventuellement substitués et d) des alkyles cycliques ou des alkyles hétérocycliques portant 5 à 7 atomes de carbones. Y est choisi indépendamment dans le groupe constitué des -NR<3>-C(O) et -C(O)-NR<3>-. X est un groupe bifonctionnel ou polyfonctionnel choisi dans le groupe constitué a) des aryles et aralkyles et b) des alkyles portant 1 à 8 atomes de carbone ayant éventuellement 1 à 3 substituants. R est -H ou alkyle inférieur, aryle inférieur et aralkyle inférieur. R' est choisi indépendamment dans le groupe constitué des -H, alkyles inférieurs portant 1 à 4 atomes de carbone, aralkyles portant de 2 à 19 atomes de carbone et de -C(O)R". R" est alkyle inférieur portant 1 à 4 atomes de carbone. Enfin, R<3> est choisi dans le groupe constitué des -H, alkyles portant 1 à 8 atomes de carbone et aralkyles portant 5 à 8 atomes de carbone.