methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate | 117462-55-2

• 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: methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate
• 英文别名: methyl 3,4;5,6-di-O-isopropylidene-2-azido-2-deoxy-D-mannate；methyl (2S)-2-azido-2-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]acetate
• CAS: 117462-55-2
• 化学式: C₁₃H₂₁N₃O₆
• 分子量: 315.326
• InChiKey: OSYLXNVUWMQXEX-UTINFBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate 在 palladium on activated charcoal 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 Dowex 50W-X₈ resin (H+ form) 、 氨 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 50.91h， 生成 1-脱氧甘露伊霉素
  参考文献：
  名称：

  合成多羟基吡咯烷和哌啶的简单方法

  摘要：

  描述了以D-葡糖醛酸-δ-内酯作为手性离析物的多羟基化哌啶和吡咯烷的短而简单的合成途径。关键的反应步骤包括用Dowex 50W-X8树脂（H +形式）选择性裂解化合物12的末端异亚丙基，环氧化物16的区域选择性开环，以及化合物14和18的分子内亲核胺化。

  DOI：

  10.1002/jhet.5570350334
• 作为产物：
  描述：

  methyl 3,4:5,6-di-O-isopropylidene-D-gluconate 在 吡啶 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate
  参考文献：
  名称：

  Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine

  摘要：

  3-epi-Casuarine, the first naturally occurring stereoisomer of casuarine, was isolated from Myrtus communis L. The glycosidase inhibition profile and NMR spectra of 3-epi-casuarine are compared with those of casuarine; the change in configuration at one of the six stereogenic centres causes a dramatic change in the conformation of the bicyclic system. The key step in the 6% overall yield synthesis of 3-epi-casuarine from D-gluconolactone is the efficient cyclization of a completely unprotected pentahydroxyaminomcsylate to the pyrrolizidine nucleus. A low yield synthesis of casuarine is also reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.005

文献信息

• [EN] SYNTHESIS OF POLYHYDROXYLATED ALKALOIDS<br/>[FR] SYNTHÈSE DES ALCALOÏDES POLYHYDROXYLÉS
  申请人：MNL PHARMA LTD

  公开号：WO2006008493A1

  公开（公告）日：2006-01-26

  A process for the production of a polyhydroxylated bicyclic (e.g. pyrrolizidine such as casuarine (10), indolizidine or quinolizidine) alkaloid comprises the cyclisation of a pyrrolidine or piperidine intermediate having three or more free hydroxyl groups.

  一种用于生产多羟基双环（例如吡咯里西啶，例如相思豆碱（10）、吲哚里西啶或喹诺里西啶）生物碱的过程，包括将具有三个或更多自由羟基的吡咯烷或哌啶中间体进行环合。
• Carbohydrate-Based Synthetic Approach to Control Toxicity Profiles of Folate−Drug Conjugates
  作者：Iontcho R. Vlahov、Hari Krishna R. Santhapuram、Fei You、Yu Wang、Paul J. Kleindl、Spencer J. Hahn、Jeremy F. Vaughn、Daniel S. Reno、Christopher P. Leamon

  DOI：10.1021/jo100448q

  日期：2010.6.4

  cysteine-loaded resin, followed by the addition of folate, deprotection, and cleavage, resulted in the isolation of the new folate−spacer: Pte-γGlu-(Glu(1-amino-1-deoxy-d-glucitol)-Glu)2-Glu(1-amino-1-deoxy-d-glucitol)-Cys-OH (21). The addition of 21 to an appropriately modified desacetylvinblastine hydrazide (DAVLBH) resulted in a conjugate (25) with an improved therapeutic index. Treatment of 25 with DTT

  为了更好地调节长春碱叶酸缀合物，EC145，新的叶酸-间隔并入1-氨基-1-脱氧的生物分布d -glucitol-γ谷氨酸亚基插入的肽主链，被合成。将Fmoc-3,4的合成5,6-二- ö异亚丙基-1-氨基-1-脱氧- d -glucitol-γ谷氨酸20，适合的Fmoc策略的固相肽合成（SPPS），是从δ-葡糖酸内酯分四个步骤实现。在半胱氨酸负载的树脂上添加交替的谷氨酸和20个部分，然后添加叶酸，脱保护和裂解，从而分离出新的叶酸间隔基：Pte-γGlu-（Glu（1-amino-1 -deoxy- d -glucitol）-Glu）2-Glu（1-氨基- 1-脱氧d -glucitol）-Cys-OH（21）。将21添加到适当修饰的去乙酰长春碱肼（DAVLBH）中产生具有改善的治疗指数的缀合物（25）。在室温下，在中性缓冲液中用DTT处理25，表明游离的DAVLBH将在内化的内体的还原环境下释放。
• CONJUGATES CONTAINING HYDROPHILIC SPACER LINKERS
  申请人：Leamon Christopher Paul

  公开号：US20100323973A1

  公开（公告）日：2010-12-23

  Described herein are compositions and methods for use in targeted drug delivery using cell receptor binding drug delivery conjugates containing hydrophilic spacer linkers for use in imaging, diagnosing, and/or treating diseases and disease states caused by pathogenic cell populations.

  本文描述了一种使用细胞受体结合药物递送共轭物质的组合物和方法，其中包含亲水性空间连接剂，用于成像、诊断和/或治疗由致病细胞群体引起的疾病和疾病状态的靶向药物递送。
• 2-Amino-2-deoxyhexoses as chiral educts for hydroxylated indolizidines. Synthesis of (+)-castanospermine and (+)-6-epicastanospermine
  作者：Marc Gerspacher、Henry Rapoport

  DOI：10.1021/jo00011a047

  日期：1991.5

  D-2-Amino-2-deoxyglucosaminic acid, obtained from D-glucosamine, and a D-2-amino-2-deoxymannosaminic acid derivative, obtained from D-glucono-delta-lactone, were derivatized and converted to the corresponding configurationally stable aldehydes. The N-(9-phenylfuoren-9-yl)-protected mannosamine derivative was readily transformed into a variety of configurationally stable alpha-amino ketones, thus providing convenient and versatile chiral educts. These educts may be envisaged as derivable from polyhydroxy alpha-amino acids. Examples of the utility of these chiral educts are provided by the efficient conversion of a D-mannosaminic acid derivative into the polyhydroxy indolizidine alkaloids (+)-castanospermine and (+)-6-epicastanospermine.
• Potential intermediates for incorporation of polyhydroxylated prolines into combinatorial libraries
  作者：Daniel D. Long、Signe M. Frederiksen、Daniel G. Marquess、Alexandra L. Lane、David J. Watkin、David A. Winkler、George W.J. Fleet

  DOI：10.1016/s0040-4039(98)01256-8

  日期：1998.8

  Bicyclic 2 and monocyclic 6 2-amino-1,4-lactones provide divergent intermediates for subsequent incorporation of polyhydroxylated prolines into combinatorial amide libraries. The X-ray crystal structure of an azidolactone, combined with molecular modelling, rationalises the very different behaviour of two azidolactones which are epimeric at a remote side-chain carbon. The conversion of 2 and 6 into DGDP 4 secures the structural claims in the paper. The enantiomers of 2 and 6 may provide access to libraries of potential inhibitors of UDP-Gal mutase and thus of mycobacterial cell wall biosynthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.