2-azido-2-deoxy-6-O-benzyl-3,4-O-isopropylidene-β-D-psico-furanose | 133886-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-azido-2-deoxy-6-O-benzyl-3,4-O-isopropylidene-β-D-psico-furanose
• 英文别名: 2-Azido-2-deoxy-3,4-O-isopropylidene-6-O-benzyl-β-D-psicofuranose；2-azido-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-psicofuranose；[(3aR,4R,6R,6aR)-4-azido-2,2-dimethyl-6-(phenylmethoxymethyl)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]methanol
• CAS: 133886-01-8
• 化学式: C₁₆H₂₁N₃O₅
• 分子量: 335.36
• InChiKey: RWVMKWZIGWGFPJ-IXYNUQLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105.91
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-azido-2-deoxy-6-O-benzyl-3,4-O-isopropylidene-β-D-psico-furanose 在 ruthenium trichloride 、 sodium periodate 作用下， 反应 0.25h， 生成 (3aR,4S,6R,6aR)-4-Azido-6-benzoyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid
  参考文献：
  名称：

  异硫氰酸根合磺酸盐，一种新型的糖基异硫氰酸盐，可用于立体控制合成巯基乙内酰脲螺核苷酸的合成

  摘要：

  硫代乙内酰脲螺核苷酸和N-烷基，芳基和糖基衍生物是通过立体控制的方式，通过氨，烷基，芳基和糖基胺与一类新的异硫氰酸根合糖的反应而制备的：甲基2-脱氧-2- isothiocyanatohex-2-ulofura（pyra）nosonates。该反应产生中间体硫脲基衍生物，其自发环化以高产率得到螺核苷。或者，由2-氨基-2-脱氧-己-2--2-氟呋喃（吡喃）磺酸甲酯和烷基，芳基和糖基异硫氰酸酯制备相同的螺核苷。一些制备的化合物具有螺硫代乙内酰脲的N-核苷的结构。

  DOI：

  10.1016/s0040-4039(01)01845-7
• 作为产物：
  描述：

  ((3aR,4R,6R,6aR)-4-Azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-trimethyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到2-azido-2-deoxy-6-O-benzyl-3,4-O-isopropylidene-β-D-psico-furanose
  参考文献：
  名称：

  Stereocontrolled synthesis of thiohydantoin spironucleosides from sugar spiroacetals

  摘要：

  5-Epithiohydantocidin, N-alkyl and N-glycosylthiohydantoin spironucleosides are prepared from glycosylaminoesters and from furanoid and pyranoid methyl isothiocyanatoulosonates. The aminoesters; and the isothiocyanates are obtained, in a stereocontrolled manner, from sugar spiroacetals through a high-yielding sequence involving ring opening with trimethyl azide, formation of an ester group, reduction of the azide, and, in the case of isothiocyanates, reaction with thiophosgene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.128

文献信息

• Synthetic studies on (+)-hydantocidin (3): a new synthetic method for construction of the spiro-hydantoin ring at the anomeric position of D-ribofuranose
  作者：Shigeru Mio、Yuko Kumagawa、Soji Sugai

  DOI：10.1016/s0040-4020(01)96124-1

  日期：——

  A facile synthetic route for the large-scale preparation of a herbicidal natural product, (+)-hydantocidin is described. The protected D-psicose 6, prepared in five steps from D-fructose, was stereospecifically converted to azido-amide 14 by N-glycosidation (TMSN3/TMSOTf), oxidation and amination. Hydantoin ring-construction on 14 was achieved by aza-Wittig reaction (PBu3/CO2/CH3CN) to give 16 without

  描述了用于大规模制备除草天然产物（+）-hydantocidin的简便合成路线。由D-果糖分五个步骤制备的被保护的D-聚乙二醇6通过N-糖基化（TMSN 3 / TMSOTf），氧化和胺化立体定向地转化为叠氮基酰胺14。乙内酰脲环在14上的结构是通过aza-Wittig反应（PBu 3 / CO 2 / CH 3 CN）得到的，在异头中心没有差向异构的情况下得到16。乙酰化后，逐步将24脱保护，从D-果糖中以16％的总收率得到（+）-hydantocidin 1。
• Unexpected Cleavage of 2-Azido-2-(hydroxymethyl)oxetanes: Conformation Determines Reaction Pathway?
  作者：Elisa Farber、Jackson Herget、José A. Gascón、Amy R. Howell

  DOI：10.1021/jo101328c

  日期：2010.11.19

  An unanticipated cleavage of 2-azido-2-(hydroxymethyl)oxetanes is reported In attempts to oxidize the title oxetanyl alcohols to the corresponding carboxylic acids with RuO4, cleaved nitriles were formed as the sole isolable products, while a closely related tetrahydrofuran gave solely the expected carboxylic acid Quantum chemical calculations suggest that the divergent outcomes are governed by conformational differences in the azidoalcohols