3-azido-1-O-tert-butyl(dimethyl)silyl-2,3,6-trideoxy-β-L-arabino-hexopyranose | 128135-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azido-1-O-tert-butyl(dimethyl)silyl-2,3,6-trideoxy-β-L-arabino-hexopyranose
• 英文别名: 3-azido-1-O-tert-butyldimethylsilyl-2,3,6-trideoxy-β-L-arabino-hexopyranose；tert-butyldimethylsilyl 3-azido-2,3,6-trideoxy-β-L-arabino-hexopyranoside；(2S,3R,4S,6R)-4-azido-6-[tert-butyl(dimethyl)silyl]oxy-2-methyloxan-3-ol
• CAS: 128135-57-9
• 化学式: C₁₂H₂₅N₃O₃Si
• 分子量: 287.434
• InChiKey: PZPUIKSYESHJIF-MMWGEVLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-azido-1-O-tert-butyl(dimethyl)silyl-2,3,6-trideoxy-β-L-arabino-hexopyranose 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 4.0h， 生成 O-methyl 3,4-diamino-2,3,4,6-tetradeoxy-α-L-lyxohexopyranoside
  参考文献：
  名称：

  铂（II）和钯（II）配合物与甲基3,4-二氨基-2,3,4,6-四脱氧-α-L-来苏-hexopyranoside

  摘要：

  开发具有以下特征的新的Pt（II）和Pd（II）配合物配体以与DNA互补的形状，我们设计并合成了甲基3,4-二氨基-2,3,4,6-四脱氧-α - L - lyxo - hexopyranoside（V）。这种合成配体 模仿形状 豆胺，存在于抗肿瘤药物中的DNA小沟结合糖部分 蒽环类抗生素 阿霉素 和 柔红霉素。 配体 V，用于形成铂（II）和Pd（II）氯化物络合物[的MC1 2（V）] 1，2，3，和4，它们具有潜在的抗肿瘤特性。我们通过以下方式对这些复合物进行了表征X射线衍射并以1 H-，13 C-，15 N-和195 Pt-核磁共振。Pt（II）和Pd（II）配合物似乎都是同构的，如X射线衍射和分子建模。配合物在晶格中形成具有短M和MMCl⋯N（H）氢键的二聚体。详细动态核磁共振在CD 2 Cl 2和CD 3 CN溶液中的研究证实了两者的单体结构溶剂以及CD 3 CN中金属周围的溶剂化和NH的分子间氢键。

  DOI：

  10.1039/b212681h
• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 咪唑 、 水 、 sodium methylate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 17.0h， 生成 3-azido-1-O-tert-butyl(dimethyl)silyl-2,3,6-trideoxy-β-L-arabino-hexopyranose
  参考文献：
  名称：

  First Preparation of Spacer-Linked Cyclic Neooligoaminodeoxysaccharides

  摘要：

  The preparation of novel cyclic 1,4-butanediol-linked oligoaminodeoxysugars 3-5 and 7 is described which are potential binders to polynucleotides. Neooligosaccharides 3-5 are assembled by two consecutive metathesis protocols. In the first phase metathesis-mediated dimerization of an aminodeoxymonosaccharide which was either allylated at the anomeric center or at C4 led to E/Z mixtures of C-2-symmetric homodimers which were transformed into the corresponding 1,4-butanediol linked disaccharides by catalytic hydrogenation of the central olefinic double bond. Double O-allylation of the head-to-head dimer set the stage for macrocyclization by means of ring-closing metathesis. This ring-closing process was highly dependent of the configuration in the carbohydrate moieties. arabino-Configured homodimer 15 directly yielded the macrocycle 32 which contains two sugar units while under the same metathesis conditions the corresponding ribo-configured starting homodimer 19 afforded cyclic neotetra- and neohexasaccharides 34 and 35 after a preceding dimerization and trimerization step, respectively. In addition, homodimer 23 was coupled with silylglycoside 14a under Lewis-acid promoted glycosidation conditions to furnish the doubly glycosylated homodimer 31. Ring-closing metathesis afforded the macrocyclic neoaminodeoxyoligosaccharide 36 with alternating 1,4-butanediol linkage and glycosidic bond. The primary cyclization products were finally transformed into the respective cyclic neoaminodeoxyoligosaccharides 3-5 and 7 by catalytic hydrogenation and standard deprotection conditions.

  DOI：

  10.1002/1521-3765(20020617)8:12<2717::aid-chem2717>3.0.co;2-p

文献信息

• A Convenient Preparation of 5-Iodo-1,4-disubstituted-1,2,3-triazole: Multicomponent One-Pot Reaction of Azide and Alkyne Mediated by CuI−NBS
  作者：Lingjun Li、Guisheng Zhang、Anlian Zhu、Lihe Zhang

  DOI：10.1021/jo800035v

  日期：2008.5.1

  The system of CuI and NBS was found to provide both I+ and Cu+ for the first time. An efficient method for preparation of 5-iodo-1,4-disubstituted-1,2,3-triazole was achieved by multicomponent one-pot reaction of azides with alkynes in the presence of the novel CuI and NBS catalytic system. The high tolerance of various sensitive groups revealed the potential applications of this method in organic

  发现CuI和NBS系统首次提供I +和Cu +。在新型CuI和NBS催化体系的存在下，通过叠氮化物与炔烃的多组分一锅反应，实现了制备5-碘-1,4-二取代-1,2,3-三唑的有效方法。各种敏感性基团的高耐受性揭示了该方法在有机合成和药物发现中的潜在应用。
• A New Synthetic Protocol for One-Pot Preparations of 5-Halo-1,4-disubstituted-1,2,3-triazoles
  作者：Lingjun Li、Yanyan Li、Ran Li、Anlian Zhu、Guisheng Zhang

  DOI：10.1071/ch11067

  日期：——

  In this paper, a new synthetic protocol for one-pot preparations of 5-halo-1,4-disubstituted-1,2,3-triazoles is provided by rational combination of a CuI catalyzed azide–alkyne cycloaddition (CuAAC) reaction and an oxidative halogenation reaction. CuI- N-chlorosuccinimide (NCS) and CuBr-NCS reaction systems are developed, respectively, for effective preparations of 5-iodo-1,4-disubstituted-1,2,3-triazoles and 5-bromo-1,4-disubstituted-1,2,3-trizoles under mild conditions with a high tolerance of various sensitive groups.

  本文通过合理结合 CuI 催化的叠氮-炔环加成反应（CuAAC）和氧化卤化反应，提供了一种一锅制备 5-卤代-1,4-二取代-1,2,3-三唑的新合成方案。CuI- N-氯代丁二酰亚胺（NCS）和 CuBr-NCS 反应体系分别用于在温和条件下有效制备 5-碘-1,4-二取代-1,2,3-三唑和 5-溴-1,4-二取代-1,2,3-三唑，对各种敏感基团具有很高的耐受性。
• A short and efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis of an anthracycline antibiotic acosaminyl-ε-iso-rhodomycinone
  作者：Bernd Renneberg、Yue-Ming Li、Hartmut Laatsch、Heinz-Herbert Fiebig

  DOI：10.1016/s0008-6215(00)00257-3

  日期：2000.12

  constituents of most anthracycline antitumour antibiotics. For an investigation of structure-activity relationships, the four diastereomeric amino sugars daunosamine, acosamine, ristosamine, and epi-daunosamine were synthesised in short and efficient routes starting from commercially available rhamnose. Several glycosyl donors were provided and their use was exemplified in the synthesis of acosaminyl-e

  3-氨基-2,3,6-三甲氧基己基吡喃糖是大多数蒽环类抗肿瘤抗生素的重要组成部分。为了研究结构-活性关系，从市售鼠李糖开始以短而有效的途径合成了四种非对映体氨基糖柔红胺，二十二胺，香豆胺和表柔红胺。提供了几种糖基供体，其用途在合成氨糖基-ε-异二十四烯酮中得到了例证。
• A Short and High Yield Access to Glycosyl Donors of Amino-Deoxy-Sugars of Biological Relevance
  作者：Laurent Daley、Carole Mouton、François Tillequin、Elisabeth Seguin、Jean-Claude Florent、Claude Monneret

  DOI：10.1080/00397919808005074

  日期：1998.1

  Synthesis of silylglycosides of 3-azido-2-deoxy-L-arabino- and ribo-hexopyranoses 4 and 5 has been achieved in 3 steps and 44,6% and 18% overall yields, respectively. The corresponding N-trifluoroacetamido derivatives 9 and 10 were further prepared in 3 steps. Usefulness of 4, 9, and 10 was demonstrated by coupling with epipodophyllotoxin derivatives or with suitably protected aminoacids such as serine or 4-OH-phenylglycine or 4-OH-phenylglycinyl glucoside.
• First Preparation of Spacer-Linked Cyclic Neooligoaminodeoxysaccharides
  作者：Guang-wu Chen、Andreas Kirschning

  DOI：10.1002/1521-3765(20020617)8:12<2717::aid-chem2717>3.0.co;2-p

  日期：2002.6.17

  The preparation of novel cyclic 1,4-butanediol-linked oligoaminodeoxysugars 3-5 and 7 is described which are potential binders to polynucleotides. Neooligosaccharides 3-5 are assembled by two consecutive metathesis protocols. In the first phase metathesis-mediated dimerization of an aminodeoxymonosaccharide which was either allylated at the anomeric center or at C4 led to E/Z mixtures of C-2-symmetric homodimers which were transformed into the corresponding 1,4-butanediol linked disaccharides by catalytic hydrogenation of the central olefinic double bond. Double O-allylation of the head-to-head dimer set the stage for macrocyclization by means of ring-closing metathesis. This ring-closing process was highly dependent of the configuration in the carbohydrate moieties. arabino-Configured homodimer 15 directly yielded the macrocycle 32 which contains two sugar units while under the same metathesis conditions the corresponding ribo-configured starting homodimer 19 afforded cyclic neotetra- and neohexasaccharides 34 and 35 after a preceding dimerization and trimerization step, respectively. In addition, homodimer 23 was coupled with silylglycoside 14a under Lewis-acid promoted glycosidation conditions to furnish the doubly glycosylated homodimer 31. Ring-closing metathesis afforded the macrocyclic neoaminodeoxyoligosaccharide 36 with alternating 1,4-butanediol linkage and glycosidic bond. The primary cyclization products were finally transformed into the respective cyclic neoaminodeoxyoligosaccharides 3-5 and 7 by catalytic hydrogenation and standard deprotection conditions.