methyl 3,4;5,6-di-O-isopropylidene-2-amino-2-deoxy-D-mannate | 133473-08-2

• 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 3,4;5,6-di-O-isopropylidene-2-amino-2-deoxy-D-mannate
• 英文别名: methyl (2S)-2-amino-2-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]acetate
• CAS: 133473-08-2
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: GKXGBGXAYSBCIE-UTINFBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3,4;5,6-di-O-isopropylidene-2-amino-2-deoxy-D-mannate 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 Dowex 50W-X₈ resin (H+ form) 、 氨 、 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， 反应 49.91h， 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 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate 在 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以70%的产率得到methyl 3,4;5,6-di-O-isopropylidene-2-amino-2-deoxy-D-mannate
  参考文献：
  名称：

  基于碳水化合物的合成方法可控制叶酸-药物共轭物的毒性

  摘要：

  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。

  DOI：

  10.1021/jo100448q

文献信息

• 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.
• Total Synthesis of Polyhydroxylated Piperidine and Pyrrolidine : Expect as Glucosidase Inhibitor
  作者：Sang-Gyeong Lee、Sang Gyeong Lee、Yong-Jin Yoon、Sung Chul Shin、Bu Yong Lee、Su-Dong Cho、Sung Kyu Kim、Ji-Hyun Lee

  DOI：10.3987/com-96-7720

  日期：——

  A new method for preparation of optically active (-)-deoxymannojirimycin (3) and 2R,5S-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (13) based on regioselective epoxide ring opening of 2-tert-butoxycarbonylamino-2-deoxy-3,4-O-isopropylidene-5,6-epoxy-D-glucitol (12) by intramolecular nucleophilic amination has been described.
• Simple synthesis of (–)-deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid via regioselective hydrolysis
  作者：Ki Hun Park、Yong Jin Yoon、Sang Gyeong Lee

  DOI：10.1039/p19940002621

  日期：——

  A short and efficient synthesis of (-)-deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is described, with D-glucono-delta-lactone as chiral educt. Key transformations included selective cleavage of a terminal isopropylidene group with Dowex 50W-X8 (H+) and intramolecular nucleophilic amination.
• FOLATE TARGETING OF NUCLEOTIDES
  申请人：Low Philip Stewart

  公开号：US20120022245A1

  公开（公告）日：2012-01-26

  The present invention relates to compounds, compositions, kits, and methods of use in targeting nucleotides, such as siRNA's, to cancer cells or to immune system cells involved in inflammation. More particularly, the invention is directed to receptor binding ligand-nucleotide delivery conjugates for use in specifically targeting the conjugates to cancer cells or to immune system cells, methods of treatment with these conjugates, methods of preparation of these conjugates, and methods of reducing the expression of a gene in vitro or in vivo with the conjugates described herein.