Phenyl 2-azido-2-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldimethylsilyl)-1-seleno-α-D-galactopyranoside | 161822-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: Phenyl 2-azido-2-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldimethylsilyl)-1-seleno-α-D-galactopyranoside
• 英文别名: [(3aR,4R,6R,7R,7aR)-7-azido-2,2-dimethyl-6-phenylselanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 161822-68-0
• 化学式: C₂₁H₃₃N₃O₄SeSi
• 分子量: 498.556
• InChiKey: YWMOAZRIBRDZGC-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Phenyl 2-azido-2-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldimethylsilyl)-1-seleno-α-D-galactopyranoside 在 n-BuNF 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 phenyl 2-azido-2-deoxy-3,4-O-isopropylidene-1-seleno-α-D-galactopyranoside
  参考文献：
  名称：

  从糖基中制备多种保护的 2-azido-2-deoxyglycopyranoses

  摘要：

  描述了从相应的糖类中制备出多种保护的 2-azido-2-deoxyglycopyranosides 的新的和有效的方法。糖基首先通过叠氮基-苯基硒基化作用转化为受保护的苯基 2-叠氮基-2-脱氧-硒基糖苷。根据存在的保护基团采用两种方法：在（二乙酰氧基碘）苯存在下制备全乙酰化糖醛（方法 A）或叠氮化三甲基甲硅烷和四正丁基氟化铵在 N-苯基硒代邻苯二甲酰亚胺用于过苄基化糖类（程序 B）。葡萄糖-甘露糖混合物 (90%) 从受保护的 d-glucal 中获得，而只有半乳糖异构体由受保护的 d-半乳醛 (75%) 形成。用 1,5-anhydro-2-deoxy-3,4-O-isopropylidene-d-lyxo-hex-l-enitol 和 1,5-anhydro-2-deoxy-3,4-O-isopropylidene-d-lyxo-hex-l-enitol 和其 6-0-乙酰基 I、6-0-烯丙基、6-0-苄基和

  DOI：

  10.1139/v95-046
• 作为产物：
  描述：

  2,6-anhydro-5-deoxy-3,4-O-isopropylidene-D-arabino-hex-5-enitol 在 咪唑 、 叠氮基三甲基硅烷 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 Phenyl 2-azido-2-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldimethylsilyl)-1-seleno-α-D-galactopyranoside
  参考文献：
  名称：

  从糖基中制备多种保护的 2-azido-2-deoxyglycopyranoses

  摘要：

  描述了从相应的糖类中制备出多种保护的 2-azido-2-deoxyglycopyranosides 的新的和有效的方法。糖基首先通过叠氮基-苯基硒基化作用转化为受保护的苯基 2-叠氮基-2-脱氧-硒基糖苷。根据存在的保护基团采用两种方法：在（二乙酰氧基碘）苯存在下制备全乙酰化糖醛（方法 A）或叠氮化三甲基甲硅烷和四正丁基氟化铵在 N-苯基硒代邻苯二甲酰亚胺用于过苄基化糖类（程序 B）。葡萄糖-甘露糖混合物 (90%) 从受保护的 d-glucal 中获得，而只有半乳糖异构体由受保护的 d-半乳醛 (75%) 形成。用 1,5-anhydro-2-deoxy-3,4-O-isopropylidene-d-lyxo-hex-l-enitol 和 1,5-anhydro-2-deoxy-3,4-O-isopropylidene-d-lyxo-hex-l-enitol 和其 6-0-乙酰基 I、6-0-烯丙基、6-0-苄基和

  DOI：

  10.1139/v95-046

文献信息

• Seleno glycosides. 2. Synthesis of Phenyl 2-(N-Acetylamino)- and 2-Azido-2-deoxy-1-seleno-.alpha.-D-glycopyranosides via Azido-phenylselenylation of Diversely Protected Glycals
  作者：S. Czernecki、E. Ayadi、D. Randriamandimby

  DOI：10.1021/jo00105a051

  日期：1994.12

  Two methods are described for the preparation of diversely protected phenyl 2-azido-2-deoxy-alpha-D-selenoglycopyranosides from protected glycals. In the first one (method A), a peracetylated glycal is treated with sodium azide and diphenyl diselenide in the presence of (diacetoxyiodo)benzene in dichloromethane at rt. With 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (tri-O-acetyl-D-glucal) an inseparable mixture of phenyl 2-azido-2-deoxy-alpha-gluco- and -alpha-manno-selenoglycosides is obtained (91% yield). With 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol (tri-O-acetyl-D-galactal) only the alpha-galacto isomer is obtained (92%). Method A is not compatible with benzyl groups. In method B, a perbenzylated glycal is reacted with trimethylsilyl azide and tetra-n-butylammonium fluoride in the presence of N-phenylselenophthalimide. From protected D-glucal a gluco/manno mixture is obtained, whereas only the galacto isomer is formed from protected D-galactal (75% yield). The compatibility of method B with a variety of protecting groups is exemplified with 6-O-acetyl, 6-O-benzyl, and 6-O-(tert-butyldimethylsilyl)-3,4-O-isopropylidene-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol. The same diastereocontrol is observed, and the alpha-D-galacto isomer is obtained (60-70% yield). Reduction of the azido group of these selenoglycosides with 1,3-propanedithiol in the presence of triethylamine and acetylation affords the corresponding phenyl 2-(N-acetylamino)-2-deoxy-alpha-D-selenoglycopyranosides in goed yield.
• Preparation of diversely protected 2-azido-2-deoxyglycopyranoses from glycals
  作者：Stanislas Czernecki、Ebtissam Ayadi

  DOI：10.1139/v95-046

  日期：1995.3.1

  6-0-tert-butyldimethylsilyl derivatives as well as with 1,s-anhydro-4,6-0-benzylidene-2-deoxy-d-lyxo- hex-1-enitol and its 3-0-acetyl and 3-0-benzyl derivatives, which were transformed into phenyl2-azido-2- deoxy-a-d-selenogalactopyranoside derivatives in good yield. In the second step, hydrolysis of these selenogly- cosi&s afforded diversely protected glycopyranoses in high yield. Peracetylated derivatives were hydrolyzed

  描述了从相应的糖类中制备出多种保护的 2-azido-2-deoxyglycopyranosides 的新的和有效的方法。糖基首先通过叠氮基-苯基硒基化作用转化为受保护的苯基 2-叠氮基-2-脱氧-硒基糖苷。根据存在的保护基团采用两种方法：在（二乙酰氧基碘）苯存在下制备全乙酰化糖醛（方法 A）或叠氮化三甲基甲硅烷和四正丁基氟化铵在 N-苯基硒代邻苯二甲酰亚胺用于过苄基化糖类（程序 B）。葡萄糖-甘露糖混合物 (90%) 从受保护的 d-glucal 中获得，而只有半乳糖异构体由受保护的 d-半乳醛 (75%) 形成。用 1,5-anhydro-2-deoxy-3,4-O-isopropylidene-d-lyxo-hex-l-enitol 和 1,5-anhydro-2-deoxy-3,4-O-isopropylidene-d-lyxo-hex-l-enitol 和其 6-0-乙酰基 I、6-0-烯丙基、6-0-苄基和