(2R,3R)-3-azido-4-(benzyloxy)butane-1,2-diol | 99884-12-5

• 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: (2R,3R)-3-azido-4-(benzyloxy)butane-1,2-diol
• 英文别名: 3-azido-4-O-benzyl-3-deoxy-D-erythritol；(2R,3R)-3-azido-4-phenylmethoxybutane-1,2-diol
• CAS: 99884-12-5
• 化学式: C₁₁H₁₅N₃O₃
• 分子量: 237.258
• InChiKey: VLEBJWDQVDHTFG-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-azido-4-(benzyloxy)butane-1,2-diol 在 sodium azide 、 sodium hydride 、 甲基磺酰氯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 ((((2R,3S)-2,4-diazidobutane-1,3-diyl)bis(oxy))bis(methylene))dibenzene
  参考文献：
  名称：

  Guanidine analogs of a deoxysugar

  摘要：

  Asymmetric syntheses of guanidine 3 and N-aminoguanidine 4 are described from (-)-epoxy alcohol 5. Compounds 3 and 4, which resemble D-glucose and D-mannose, were designed as generic hexopyranose substitutes and represent new templates for assembling glycomimetic structures.

  DOI：

  10.1016/0040-4039(94)02392-o
• 作为产物：
  描述：

  3-azido-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-D-erythritol 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以82%的产率得到(2R,3R)-3-azido-4-(benzyloxy)butane-1,2-diol
  参考文献：
  名称：

  脯氨酸催化的醛醇缩合反应的双重不对称诱导的起源。

  摘要：

  已经使用HF / 6-31G（d）计算进行了计算研究，以阐明脯氨酸催化的羟醛反应的双重不对称诱导的起源。计算的过渡结构解释了获得的实验数据。

  DOI：

  10.1021/jo800934b

文献信息

• Regiochemical control of the ring opening of 1:2-epoxides by means of chelating processes. 10. Synthesis and ring opening reactions of mono- and difunctionalized cis and trans aliphatic oxirane systems
  作者：Francesca Azzena、Federico Calvani、Paolo Crotti、Cristina Gardelli、Franco Macchia、Mauro Pineschi

  DOI：10.1016/0040-4020(95)00633-j

  日期：1995.9

  The regiochemical outcome of the ring opening of 1:2-epoxides through chelation processes assisted by metal ions, was verified in mono- and difunctionalized aliphatic oxirane systems bearing the heterofunctionality (OR) in an homoallylic and/or allylic relationship to the oxirane ring. The effect of the distance of the OR functionality from the oxirane ring and of the type of protective group on the

  通过单官能和双官能的脂族环氧乙烷体系在与环氧乙烷环呈均烯丙基和/或烯丙基关系的杂官能度（OR）中验证了通过金属离子辅助的螯合过程使1：2-环氧化物开环的区域化学结果。检查了OR官能团与环氧乙烷环的距离以及保护基类型对这些系统的区域化学结果的影响。在某些情况下，使用LiClO 4或Mg（ClO 4）2作为促进金属盐使得有可能获得良好的区域交替方法。
• The C2 Selective Nucleophilic Substitution Reactions of 2,3-Epoxy Alcohols Mediated by Trialkyl Borates:  The First <i>endo</i>-Mode Epoxide-Opening Reaction through an Intramolecular Metal Chelate
  作者：Minoru Sasaki、Keiji Tanino、Atsushi Hirai、Masaaki Miyashita

  DOI：10.1021/ol034455f

  日期：2003.5.1

  [reaction: see text] Highly efficient C2 selective substitution reactions of 2,3-epoxy alcohols with nucleophiles were developed by using NaN(3)-(CH(3)O)(3)B, NaSPh-(CH(3)O)(3)B, or NaCN-(C(2)H(5)O)(3)B system. The reaction proceeds through novel endo-mode epoxide opening of an intramolecular boron chelate, which was suggested from both experimental and quantum mechanic studies.

  [反应：参见文本]通过使用NaN（3）-（CH（3）O）（3）B，NaSPh-（CH（3）O）开发了2,3-环氧醇与亲核试剂的高效C2选择取代反应）（3）B或NaCN-（C（2）H（5）O）（3）B系统。该反应通过分子内硼螯合物的新型内模环氧化物开口而进行，这是从实验和量子力学研究中提出的。
• Synthesis of Optically Pure 2-Aziridinemethanols: Versatile Synthetic Building Blocks.
  作者：Nobutaka FUJII、Kazuo NAKAI、Hiromu HABASHITA、Yuka HOTTA、Hirokazu TAMAMURA、Akira OTAKA、Toshiro IBUKA

  DOI：10.1248/cpb.42.2241

  日期：——

  Synthesis of three cis-trans pairs of N-sulfonylated-2-aziridinemethanols starting from (S)-threonine, (R)-allothreonine, a chiral 2-amino alcohol, or enantiomerically enriched 2, 3-epoxy alcohols is described. A synthetic route to N-tosyl- and N-mesyl-2-aziridinemethanols from (R)- and (S)-serines is also presented.

  介绍了从(S)-苏氨酸、(R)-全苏氨酸、手性 2-氨基醇或对映体富集的 2，3-环氧醇出发，合成三对顺反异构的 N-磺酰基-2-氮丙啶甲醇。此外，还介绍了从(R)-和(S)-丝氨酸合成 N-对甲基苯磺酰-和 N-甲磺酰-2-氮丙啶甲醇的合成路线。
• Solid-supported sodium azide reagents: their preparation and reactions with epoxides
  作者：Makoto Onaka、Keisuke Sugita、Yusuke Izumi

  DOI：10.1021/jo00266a023

  日期：1989.3
• A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-d-arabinitol using Co(III)(salen)-catalyzed hydrolytic kinetic resolution of a two-stereocentered anti-azido epoxide
  作者：Rambabu N. Reddi、Pragati K. Prasad、Rupali G. Kalshetti、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2016.10.013

  日期：2017.1

  A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol, (+)-DAB-1, has been described in good overall yield (18.1%) and with high enantiomeric purity (up to 98% ee) starting from a simple raw material, cis-2-butene-1,4-diol. The Co-catalyzed hydrolytic kinetic resolution of a two-stereocentered racemic azido epoxide followed by asymmetric dihydroxylation of the alkene and 'one pot' reductive cyclisation of the azido diol are key reactions in the synthetic sequence. (C) 2016 Elsevier Ltd. All rights reserved.