1,2,3,4-tetra-O-benzoyl-6-desoxy-α-L-mannopyranose

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4-tetra-O-benzoyl-6-desoxy-α-L-mannopyranose
• 英文别名: 1,2,3,4-Tetra-O-benzoyl-α-L-rhamnopyranose；L-rhamnopyranose tetrabenzoate；1,2,3,4-tetra-O-benzoyl-6-deoxy-α-L-mannopyranose；1,2,3,4-tetra-O-benzoyl-L-rhamnopyranose；Tetra-O-benzoyl-α-L-rhamnopyranose；1,2,3,4-tetra-O-bensyl-α-L-rhamnopyranose；1,2,3,4-tetra-O-benzoyl-L-rhamnopyranoside；α-L-rhamnopyranose tetrabenzoate；[(2S,3S,4R,5R,6S)-4,5,6-tribenzoyloxy-2-methyloxan-3-yl] benzoate
• 化学式: C₃₄H₂₈O₉
• 分子量: 580.591
• InChiKey: RLJCRSFLYYQNAK-KHTCUILWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-benzoyl-6-desoxy-α-L-mannopyranose 在 氢溴酸 、 溶剂黄146 作用下， 生成 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide
  参考文献：
  名称：

  The Reaction of Tribenzoyl-α-L-rhamnopyranosyl Bromide with Methanol. Various Benzoylated Derivatives of L-Rhamnose

  摘要：

  DOI：

  10.1021/ja01145a097
• 作为产物：
  描述：

  莰菲醇-3-O-芸香糖苷 在 盐酸 、 laccase (EC 1.10.3.2) from Pycnoporus cinnabarinus 、 水 作用下， 以 甲醇 、 水 为溶剂， 反应 2.25h， 生成 1,2,3,4-tetra-O-benzoyl-6-desoxy-α-L-mannopyranose
  参考文献：
  名称：

  UNIQUE PHENYL ETHER TYPE BIFLAVONOIDS, ZIZYFLAVOSIDES A AND B WITH BIOMIMETIC SYNTHESIS FOR ZIZYFLAVOSIDE A

  摘要：

  During our investigation of Zizyphus spina-christi (L.) Willd. leaves for anti-inflammatory activity, eight compounds were characterized. Two are new phenyl ether type biflavonoids, which were assigned as zizyflavosides A (1) and B (2). The structures of 1 and 2 were determined by spectroscopic analyses including ID, 2D NMR and MS spectroscopic and chemical data. The other isolated compounds were known flavonoids kaempferol-3-O-rutinoside (5), quercetin-3-O-rutinoside (6), 3`,5`-di-C-beta-D-glucosylphloretine (7), quercetin-3-O-[beta-D-xylosyl-(1 -> 2)-alpha-L-rhamnoside]-4`-O-alpha-L-rhamnoside (8), epiafzelechin (9) and quercetin-3-O-[beta-D-xylosyl-(1 -> 2)-alpha-L-rhamnoside] (10). Zizyflavoside A was synthesized from quercetin-3-O-rutinoside and kaempferol-3-O-rutinoside using laccase as an enzyme and this biomimetic synthesis could be indication to its biosynthetic pathway.

  DOI：

  10.3987/com-10-12002

文献信息

• Practical synthesis of latent disarmed S-2-(2-propylthio)benzyl glycosides for interrupted Pummerer reaction mediated glycosylation
  作者：Yang Xu、Qian Zhang、Ying Xiao、Pinru Wu、Wei Chen、Zejin Song、Xiong Xiao、Lingkui Meng、Jing Zeng、Qian Wan

  DOI：10.1016/j.tetlet.2017.05.014

  日期：2017.6

  Practical synthetic methods to latent disarmed S-2-(2-propylthio)benzyl (SPTB) glycosides for interrupted Pummerer reaction mediated glycosylation have been discovered. Among them, both coupling reaction of PTB-Cl with glycosyl thiols and BF3·OEt2 promoted reaction of peracylated glycosides with PTB-SH produced peracylated SPTB glycosides in large scales and with high efficiency.

  已经发现了潜在的解除武装的S -2-（2-丙硫基）苄基（SPTB）糖苷用于中断的Pummerer反应介导的糖基化的实用合成方法。其中，PTB-Cl与糖基硫醇的偶联反应和BF 3 ·OEt 2均促进了过酰化的糖苷与PTB-SH的反应，从而大规模，高效地生产了过酰化的SPTB糖苷。
• Visible Light Enables Aerobic Iodine Catalyzed Glycosylation
  作者：Matthias Krumb、Tobias Lucas、Till Opatz

  DOI：10.1002/ejoc.201900143

  日期：2019.7.31

  and readily available photocatalyst was developed. Oxygen serves as a green and cost‐efficient terminal oxidant and irradiation is performed with a common household LED bulb. The scope of this glycosylation protocol was investigated in the synthesis of O‐glycosides with yields up to 95 %.

  开发了一种通用的方案，该方案使用碘作为廉价且容易获得的光催化剂来光诱导硫糖苷的催化活化。氧气是一种绿色且具有成本效益的终端氧化剂，并且使用普通的家用LED灯泡进行辐照。在O-糖苷的合成中研究了这种糖基化方案的范围，产率高达95％。
• 1,2-<i>Trans</i>-Selective Synthesis of Glycosyl Boranophosphates and Their Utility as Building Blocks for the Synthesis of Phosphodiester-Linked Disaccharides
  作者：Kazuki Sato、Natsuhisa Oka、Shoichi Fujita、Fumiko Matsumura、Takeshi Wada

  DOI：10.1021/jo902725g

  日期：2010.4.2

  is controlled by neighboring group participation. The resultant glycosyl boranophosphate triesters were converted into the corresponding boranophosphate diesters and condensed with appropriately protected monosaccharides to give disaccharides linked with an anomeric boranophosphate linkage. Furthermore, the disaccharides worked as precursors of the corresponding phosphodiester-linked disaccharides

  高度1,2-反式通过二甲基硼酸磷酸酯与糖基碘化物的糖基化反应，开发了糖基硼酸磷酸酯衍生物的选择性合成方法。对反应机理的研究表明，反应的立体选择性受相邻基团的参与控制。将所得的糖基硼磷酸三酯转变为相应的硼磷酸二酯，并与适当保护的单糖缩合，得到与异头硼磷酸酯键连接的二糖。此外，二糖充当相应的磷酸二酯连接的二糖的前体。硼酸磷酸酯连接的二糖的完整合成及其向磷酸二酯连接的二糖的转化均以高收率完成，而在端基异构体位置没有损失立体纯度，
• [EN] 6R-(3,6-DIDEOXY-L-ARABINO-HEXOPYRANOSYLOXY)HEPTANOIC ACID, PREPARATION PROCESS FOR THE SAME AND DAUER EFFECT THEREOF<br/>[FR] ACIDE 6R-(3,6-DIDESOXY-L-ARABINO-HEXOPYRANOSYLOXY)HEPTANOIQUE, PROCEDE DE PREPARATION DE CET ACIDE ET EFFET DAUER DE CET ACIDE
  申请人：JUNG MANKIL

  公开号：WO2005075491A1

  公开（公告）日：2005-08-18

  The present invention relates to a determination of a stereochemistry, a synthesis and dauer effect of 6R-(3,6-dideoxy-L-arabino-hexopyranosyloxy) heptanoic acid as a pheromone isolated from the Caenorhabditis elegance related to suppress of aging and stress. It becomes possible to develop medical substances using the pheromone relating to aging, stress, metabolism, signal transfer system in vivo, and anti-cancer, obesity and a suppressing agent for aging and stress.

  本发明涉及一种从Caenorhabditis elegans中分离出的6R-(3,6-二去氧-L-阿拉伯糖基)庚酸酯素的立体化学确定、合成和抑制老化和应激的效果。利用与老化、应激、新陈代谢、体内信号传递系统以及抗癌、肥胖和抑制老化和应激的药剂相关的这种信息素，可以研发出医药物质。
• Synthesis of oleanolic disaccharide derivatives
  作者：Shu Chen Pei、Jian Bo Wu、Fan Lei、Shan Qian、Li Hai、Yong Wu

  DOI：10.1016/j.cclet.2012.01.022

  日期：2012.4

  and possesses many attractive biological activities. Recently, some oleanolic derivatives were reported to have interesting anti-tumor activities. Herein, using association principle of drug design, OA disaccharide 17 was designed and synthesized by coupling a-L -rhamnopyranosyl-(1→2)- a-L -arabinopyranosyl disaccharide moiety, which has proved to be a unique sugar sequence with strongly antitumor

  摘要齐墩果酸1广泛存在于食品，药材等植物中，并具有许多诱人的生物学活性。最近，据报道一些齐墩果酸衍生物具有有趣的抗肿瘤活性。在此，利用药物设计的结合原理，通过偶联αL-鼠李糖基-（1→2）-αL-阿拉伯吡喃糖基二糖部分，设计合成了OA二糖17，其已被证明是具有强抗肿瘤活性的独特糖序列，并被修饰。在C-17上带有腈的OA。