ethyl 2,3,6-tri-O-acetyl-4-azido-4-deoxy-α-D-mannopyranoside | 864852-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,6-tri-O-acetyl-4-azido-4-deoxy-α-D-mannopyranoside
• 英文别名: [(2S,3R,4S,5S,6S)-4,5-diacetyloxy-3-azido-6-ethoxyoxan-2-yl]methyl acetate
• CAS: 864852-13-1
• 化学式: C₁₄H₂₁N₃O₈
• 分子量: 359.336
• InChiKey: MCMBJKMXQLDXPZ-DGTMBMJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,6-tri-O-acetyl-4-azido-4-deoxy-α-D-mannopyranoside 、 1,3,5-三乙炔苯 在 copper diacetate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以80%的产率得到1,3,5-tris[4-(ethyl 2,3,6-tri-O-acetyl-4-deoxy-α-D-mannopyranosid-4-yl)-1H-1,2,3-triazol-1-yl]benzene
  参考文献：
  名称：

  Efficient Synthesis of Some Unsaturated [1,2,3]‐Triazole‐Linked Glycoconjugates

  摘要：

  Thermal 1,3-dipolar cycloaddition of ethyl 4-azido-2,3,4-trideoxy-alpha-D- erythro -hex-2-enopyranosides with diethyl acetylenedicarboxylate or copper-catalyzed reaction with various functionalized alkynes gave the corresponding 1-(ethyl 2,3,4-trideoxy-alpha-D- erythro -hex-2-enopyranosid-4-yl)-1 H -1,2,3-triazole derivatives in quite good yields. These unsaturated compounds could be transformed into 1-(ethyl 2,3-di-O-acetyl-4-deoxy-alpha-D-mannopyranosid-4-yl)-1 H -1,2,3-triazoles by a simple dihydroxylation reaction. Copper-catalyzed condensation of ethyl 6-O-acetyl-4-azido-2,3,4-trideoxy-alpha-D- erythro-hex-2-enopyranoside with 1,3,5-triethynylbenzene or 1,3,5-tris(prop-2-ynyloxy)benzene afforded the corresponding trivalent glycoconjugate clusters.

  DOI：

  10.1080/07328300600803484
• 作为产物：
  描述：

  ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 在 四氧化锇 、 四(三苯基膦)钯 、 sodium azide 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 25.0h， 生成 ethyl 2,3,6-tri-O-acetyl-4-azido-4-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Stereocontrolled palladium(0)-catalyzed preparation of unsaturated azidosugars: an easy access to 2- and 4-aminoglycosides

  摘要：

  The palladium-catalyzed substitution of alkyl 4,6-di-O-acetyl-alpha-D-erythro-hex-2-eno-pyranosides using NaN3 as the nucleophile gave predominantly the corresponding alkyl 2-azido-2,3,4-trideoxy-alpha-D-threo-hex-2-enopyranosides in the presence of Pd(PPh3)(4). However, alkyl 6-O-acetyl-4-azido-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranosi des were obtained as the major products using Pd(PPh3)4 as the catalyst in the presence of dppb as the added ligand. Conversely, alkyl 6-O-(tert-butyidimethylsilyl)-4-0-methoxycarbonyl-2,3-dideoxy-alpha-D-hex-2-enopyranosides gave exclusively alkyl 4-azido-6-O-(tert-butyldimethylsilyi)-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranosides in the presence of Pd-2(dba)(3)/PPh3 as the catalyst and Me3SiN3 as the nucleophile. The bis-hydroxylation followed by hydrogenation of ethyl 4-azido-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranoside afforded the corresponding 4-amino-alpha-D-mannopyranoside, when propyl 2-azido-2,3,4-trideoxy-alpha-D-threo-hex-3-enopyranoside gave the 2-amino-alpha-D-altropyranoside under the same conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.041