1,6:2,3-Dianhydro-4-deoxy-β-D-ribo-hexopyranose | 40838-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 1,6:2,3-Dianhydro-4-deoxy-β-D-ribo-hexopyranose
• 英文别名: (1R,2R,4R,6S)-3,8,9-trioxatricyclo[4.2.1.02,4]nonane
• CAS: 40838-15-1
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: SEBDBMNJCRNXLL-SLPGGIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,6:2,3-Dianhydro-4-deoxy-β-D-ribo-hexopyranose 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 氯化铵 作用下， 以 四氢呋喃 、 乙二醇甲醚 为溶剂， 反应 85.0h， 生成 endo-1,6-anhydro-2,3,4-trideoxy-2,3-epimino-β-D-lyxo-hexopyranose
  参考文献：
  名称：

  Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra

  摘要：

  通过锂铝氢还原相邻的trans偶氮基对甲苯磺酸酯，制备了一系列1,6-脱水-β-D-己糖苷的2,3,4-三去氧-2,3-表胺和2,3,4-三去氧-3,4-表胺衍生物。观察到从反应基团的trans-二赤道排列的前体中形成环氮丙烷的不寻常现象。讨论了环氮丙烷的NMR和红外光谱。

  DOI：

  10.1135/cccc20041939
• 作为产物：
  描述：

  1,-脱水-3,-O-异丙二烯-β-D-谷氨酸五乙酸酯 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.17h， 生成 1,6:2,3-Dianhydro-4-deoxy-β-D-ribo-hexopyranose
  参考文献：
  名称：

  Reactions of some pyranoside diol monotriflates with nucleophiles and bases

  摘要：

  Reaction of pyranoside diol (equatorial) monotriflates with soft, nonbasic nucleophiles is a useful way to make axial heteroatom-substituted and ''epimerized'' pyranosides, particularly where a fused acetal ring inhibits ring contraction. Among the substrates examined (1, 2,3,4,35), only 4 shows a strong tendency to give ring-contracted products. The reaction of 1-3 with more basic nucleophiles (F-, t-BuO-) leads to the anhydrosugars 8, 25, and 26, respectively. The S(N)2 reaction of 35 with tetra-n-butylammonium iodide forms the basis for a new synthesis of the Cerny epoxide 32.

  DOI：

  10.1021/jo00052a058

文献信息

• An Ezomycin Model Glycosylation
  作者：Spencer Knapp、Carlos Jaramillo、Brett Freeman

  DOI：10.1021/jo00096a022

  日期：1994.8

  A model glycosylation reaction for application to the synthesis of the ezomycin class of antibiotics is described. The ezoaminuroic thioglycoside donor 13, with a reduced and protected C-6 position and trifluoroacetamide at C-3, was prepared from the Cerny epoxide 7 by a nine-step procedure. The model D-pulo-pyranoside acceptor 20, which closely resembles an actual acceptor in the vicinity of the reacting axial hydroxyl, was synthesized from methyl beta-D-galactopyranoside 14. Glycosylation with N-iodosuccinimide/triflic acid as promoter gave the disaccharide 21 in 90% yield.
• Free radical reactions of carbohydrate derivatives in the synthesis of carbocyclic compounds. 1. Intramolecular C2?C6 cyclization of monosaccharides ? A new route to substituted cyclopentanes
  作者：A. F. Sviridov、N. K. Kochetkov

  DOI：10.1007/bf00863074

  日期：1992.3

  The feasibility of adopting a new approach to the preparation of chiral carbocyclic compounds has been demonstrated by experiment. Synthesis was achieved by way of intramolecular free radical C2-C6 cyclization of carbohydrate derivatives, which produced compounds with quaternary C2 carbon atom having a strictly defined configuration.
• Chemical synthesis of 4-deoxy-(1→6)-α-d-xylo-hexopyranan and 3,4-dideoxy-(1→6)-α-d-erythro-hexopyranan
  作者：Masahiko Okada、Ayako Banno、Hiroshi Sumitomo

  DOI：10.1016/0008-6215(92)84083-5

  日期：1992.3
• Reactions of some pyranoside diol monotriflates with nucleophiles and bases
  作者：Spencer Knapp、Andrew B. J. Naughton、Carlos Jaramillo、Brenda Pipik

  DOI：10.1021/jo00052a058

  日期：1992.12

  Reaction of pyranoside diol (equatorial) monotriflates with soft, nonbasic nucleophiles is a useful way to make axial heteroatom-substituted and ''epimerized'' pyranosides, particularly where a fused acetal ring inhibits ring contraction. Among the substrates examined (1, 2,3,4,35), only 4 shows a strong tendency to give ring-contracted products. The reaction of 1-3 with more basic nucleophiles (F-, t-BuO-) leads to the anhydrosugars 8, 25, and 26, respectively. The S(N)2 reaction of 35 with tetra-n-butylammonium iodide forms the basis for a new synthesis of the Cerny epoxide 32.
• Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra
  作者：Jindřich Karban、Miloš Buděšínský、Jiří Kroutil

  DOI：10.1135/cccc20041939

  日期：——

  A complete series of 2,3,4-trideoxy-2,3-epimino and 2,3,4-trideoxy-3,4-epimino derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminium hydride reduction of vicinal trans azido tosylates. Unusual formation of the aziridine ring from precursors with the trans-diequatorial arrangement of the reacting groups was observed. NMR and infrared spectra of the aziridines are discussed.

  通过锂铝氢还原相邻的trans偶氮基对甲苯磺酸酯，制备了一系列1,6-脱水-β-D-己糖苷的2,3,4-三去氧-2,3-表胺和2,3,4-三去氧-3,4-表胺衍生物。观察到从反应基团的trans-二赤道排列的前体中形成环氮丙烷的不寻常现象。讨论了环氮丙烷的NMR和红外光谱。