methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranoside | 7511-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranoside
• 英文别名: methyl tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranoside；methyl tri-O-acetyl-6-deoxy-6-iodo-β-D-glycopyranoside；methyl 2,3,4-tri-O-acetyl-6-iodo-β-D-glucopyranoside；methyl-[tri-O-acetyl-6-iodo-6-deoxy-β-D-glucopyranoside；Methyl-[tri-O-acetyl-6-jod-6-desoxy-β-D-glucopyranosid；Methyl 2,3,4-tri-o-acetyl-6-deoxy-6-iodo-beta-d-glucopyranoside；[(2S,3S,4S,5R,6R)-4,5-diacetyloxy-2-(iodomethyl)-6-methoxyoxan-3-yl] acetate
• CAS: 7511-38-8
• 化学式: C₁₃H₁₉IO₈
• 分子量: 430.194
• InChiKey: WKINNAVZJINYDX-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranoside 在 sodium 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.58h， 生成
  参考文献：
  名称：

  D-葡萄糖的一些衍生物的氟化（C5）

  摘要：

  β-D-吡喃葡萄糖和α-和β-D-吡喃葡萄糖基氟的各种过酯的光溴化反应产生了能够转化为相应的5-氟化物的5-溴衍生物。发现这种转化的最佳试剂是乙醚/二氯甲烷中的四氟硼酸银。介绍了五-O-苯甲酰基-5-氟-α-L-吡喃糖的单晶X射线结构测定。此外，还开发了5-氟吡喃糖苷的各种方法。苯基四-O-乙酰基-β-D-吡喃葡萄糖苷的光溴化作用，随后氟化和保护基团的去除得到苯基5-氟-β-D-吡喃葡萄糖苷。五-O-乙酰基-β-D-吡喃葡萄糖的光溴化，然后水解和甲醇处理，得到半缩醛，该半缩醛通过用二乙基氨基三氟化硫处理转化，随后保护基团去除为甲基5-氟-β-D-吡喃葡萄糖苷。甲基 2,3,4-tri-O-benzyl-6-deoxy-α- 和 -β-D-xylo-hex-5-enosides 用二甲基二环氧乙烷或 3-氯过苯甲酸转化为相应的环氧化物；随后用氟化氢/吡啶处理，然后产生5-氟吡喃糖苷作为主要产物。介绍了

  DOI：

  10.1071/ch03288
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-glucopyranoside 在 丙酮 、 sodium iodide 作用下， 生成 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranoside
  参考文献：
  名称：

  The Unimolar Tosylation¹ of alpha- and beta-Methyl-d-glucosides

  摘要：

  DOI：

  10.1021/ja01269a045

文献信息

• TARGETED PEPTIDE CONJUGATES
  申请人：Marker Gene Technologies, Inc.

  公开号：US20180207287A1

  公开（公告）日：2018-07-26

  The present invention relates to the preparation and use of therapeutic compounds for the treatment of diseases at specific subcellular target areas such as specific cellular organelles. In particular, the therapeutic compounds of the invention are specific for modifying enzyme activity within targeted organelles or structures of cells and tissues. Subcellular organelles and structures that may be specifically targeted by compounds of the present invention include lysosomes, autophagasomes, the endoplasmic reticulum, the Golgi complex, peroxisomes, the nucleus, membranes and the mitochondria.

  本发明涉及制备和使用治疗化合物，用于治疗特定亚细胞靶区域的疾病，如特定细胞器。具体来说，本发明的治疗化合物特异地用于修改靶向细胞和组织的细胞器或结构内的酶活性。本发明的化合物可以特异地靶向的亚细胞器和结构包括溶酶体、自噬体、内质网、高尔基体、过氧化物酶体、细胞核、细胞膜和线粒体。
• An Expeditious Synthesis of Iminosugars
  作者：Michael N. Gandy、Matthew J. Piggott、Keith A. Stubbs

  DOI：10.1071/ch10211

  日期：——

  A short and expedient synthesis of the potent glycosidase inhibitors, 1-deoxynojirimycin, miglitol, miglustat, 1-deoxymannojirimycin, and 1-deoxygalactonojirimycin is presented.

  本文介绍了强效糖苷酶抑制剂 1-脱氧野尻霉素、米格列醇、米格鲁司他、1-脱氧甘露尻霉素和 1-脱氧半乳糖尻霉素的简捷合成方法。
• Formation of 6-deoxy-6-iodohexopyranosides as substrates for the hex-5-enose degradation
  作者：Gerald O. Aspinall、Roshan C. Carpenter、Lev Khondo

  DOI：10.1016/0008-6215(87)80105-2

  日期：1987.8

  and poly-saccharide derivatives. It is shown that ( 1 ) unsubstituted d -glucopyranosides undergo selective, primary iodination without unwanted side-reactions; ( 2 ) primary iodination of d -galactopyranosides is accompanied by 3,6-anhydride formation, so that the desired reaction is only possible with protection of secondary hydroxyl groups; and ( 3 ) the extent of iodination in substrates of higher

  摘要研究了一系列单，双和多糖衍生物的6-脱氧-6-碘己吡喃果糖苷作为六-戊糖降解的潜在底物的合成方法。结果表明：（1）未取代的d-吡喃葡萄糖苷经过选择性的初级碘化反应而没有不希望的副反应。（2）d-吡喃半乳糖苷的初级碘化反应伴随着3，6-酐的形成，因此所需的反应只有在保护仲羟基的情况下才有可能。（3）通过使乙酰化的（或甲基化的）衍生物与三丁基锡烷反应，然后分析所得的6-脱氧己吡喃糖苷，方便地确定较高分子量的底物中的碘化程度。
• Process for production of aromatic compounds
  申请人：Nakamura Masaharu

  公开号：US20070123734A1

  公开（公告）日：2007-05-31

  A problem of the present invention is to provide an economical process with minimized toxicity for producing an aromatic compound having a variety of substituents such as various alkyl groups, and the problem is solved by a process for production of an aromatic compound represented by formula (1) below, which comprises reacting a compound represented by formula (2) below with an aromatic magnesium reagent represented by formula (3a) below in the presence of an iron catalyst and a diamine compound: wherein R is an optionally substituted hydrocarbon group or a C 3 -C 10 saturated or unsaturated ring group; A is an optionally substituted C 4 -C 20 aromatic group or an optionally substituted heteroaromatic group; X is a halogen atom or a sulfonic acid ester; and Y 1 is bromine, iodine, chlorine or a carbanion ligand.

  本发明的问题是提供一种经济的过程，最小化毒性，用于生产具有各种取代基（例如各种烷基）的芳香化合物，该问题通过以下公式（1）所代表的芳香化合物的生产过程得到解决，其中，在铁催化剂和二胺化合物的存在下，将以下公式（2）所代表的化合物与以下公式（3a）所代表的芳香基镁试剂反应：其中，R是可选的取代的碳氢化合物基团或C3-C10饱和或不饱和环基团；A是可选的取代的C4-C20芳香基团或可选的取代的杂环芳基团；X是卤素原子或磺酸酯；Y1是溴、碘、氯或碳阴离子配体。
• PROCESS FOR PRODUCTION OF AROMATIC COMPOUNDS
  申请人：Japan Science and Technology Agency

  公开号：EP1724248A1

  公开（公告）日：2006-11-22

  A problem of the present invention is to provide an economical process with minimized toxicity for producing an aromatic compound having a variety of substituents such as various alkyl groups, and the problem is solved by a process for production of an aromatic compound represented by formula (1) below, which comprises reacting a compound represented by formula (2) below with an aromatic magnesium reagent represented by formula (3a) below in the presence of an iron catalyst and a diamine compound: wherein R is an optionally substituted hydrocarbon group or a C3 - C10 saturated or unsaturated ring group; A is an optionally substituted C4 - C20 aromatic group or an optionally substituted heteroaromatic group; X is a halogen atom or a sulfonic acid ester; and Y1 is bromine, iodine, chlorine or a carbanion ligand.

  本发明的一个问题是为生产具有各种取代基（如各种烷基）的芳香族化合物提供一种经济的、毒性最小的工艺，该问题是通过一种生产下式（1）所代表的芳香族化合物的工艺来解决的，该工艺包括在铁催化剂和二胺化合物存在下，使下式（2）所代表的化合物与下式（3a）所代表的芳香族镁试剂反应： 其中 R 是任选取代的烃基或 C3 - C10 饱和或不饱和环基；A 是任选取代的 C4 - C20 芳香族基团或任选取代的杂芳香族基团；X 是卤素原子或磺酸酯；Y1 是溴、碘、氯或碳阴离子配位体。