1,2:5,6-di-O-isopropylidene-3-C-but-1-enyl-α-D-glucofuranose | 182816-78-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-3-C-but-1-enyl-α-D-glucofuranose
• 英文别名: (3aR,5R,6S,6aR)-6-but-3-enyl-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 182816-78-0
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: CJYDKTKCNOWJNO-VBTGVMJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-C-but-1-enyl-α-D-glucofuranose 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium periodate 、 硫酸 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 环己烯 、 正丁醇 为溶剂， 反应 51.42h， 生成 (1S,2S,3S,5S)-3-<(6-chloro-5-aminopyrimidin-4-yl)amino>-1-(hydroxymethyl)cycloheptane-1,2,5-triol
  参考文献：
  名称：

  Chiral Carbocyclic Nucleosides from d-Glucose:  Enantiodivergent Synthesis and One-Pot Entry of Dimethylamino Functionality in the Purine Rings

  摘要：

  Cyclization of appropriately designed enose-nitrones derived from D-glucose, having nitrone at C-5 or C-l and allylic/homoallylic functionalities at C-3 of the sugar backbone, afforded polyhydroxylated aminocarbocycles which were subsequently used as the precursors for carbocyclic nucleoside analogues (11, 13, 16, 21, and 23). The enantiodirecting synthesis of both the enantiomeric pairs of nucleoside analogues 11 and 13, 21a and 23a, and 21c and 23c, has also been demonstrated by judiciously applying intramolecular nitrone cycloaddition (INC) reaction. An interesting observation was that in the cyclization reaction of pyrimidine ring to purine ring in DMF solvent, the substitution of C-6 chloro group with a dimethylamino functionality also occurred spontaneously under mild condition, though similar reactions are reported to occur at higher temperature. The hydrogen bonding between N-3 of the purine ring and an appropriate hydroxy substituent in the carbocycle seems to play a crucial role in this reaction.

  DOI：

  10.1021/jo981955r
• 作为产物：
  描述：

  3,3'-anhydro-3-C-hydroxymethyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 、 烯丙基溴化镁 以 四氢呋喃 为溶剂， 反应 12.0h， 以72%的产率得到1,2:5,6-di-O-isopropylidene-3-C-but-1-enyl-α-D-glucofuranose
  参考文献：
  名称：

  获得光学活性，功能化的五元，六元和七元碳环衍生物的简单途径

  摘要：

  用作非天然生物活性手性碳环核苷和糖苷酶抑制剂的前体的异恶唑烷碳环衍生物6、7和13已经由D-葡萄糖通过分子内的1,3-偶极环加成合成。

  DOI：

  10.1016/0040-4020(96)00652-7

文献信息

• Application of Intramolecular Nitrone Cycloaddition Reaction:  Synthesis of Chiral Aminocarbocycles and Carbocyclic Nucleosides from Carbohydrate Precursors
  作者：Narayan C. Bar、Atanu Roy、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1021/jo971342z

  日期：1997.12.1
• A simple route to optically active, functionalized five-, six- and seven-membered carbocyclic derivatives
  作者：Ranjan Patra、Narayan C. Bar、Atanu Roy、Basudeb Achari、Nanda Ghoshal、Sukhendu B. Mandal

  DOI：10.1016/0040-4020(96)00652-7

  日期：1996.8

  The isoxazolidinocarbocyclic derivatives 6, 7 and 13, useful as precursors for unnatural bioactive chiral carbocyclic nucleosides and for glycosidase inhibitors have been synthesized from D-glucose through intramolecular 1,3-dipolar cycloaddition.

  用作非天然生物活性手性碳环核苷和糖苷酶抑制剂的前体的异恶唑烷碳环衍生物6、7和13已经由D-葡萄糖通过分子内的1,3-偶极环加成合成。
• Chiral Carbocyclic Nucleosides from <scp>d</scp>-Glucose:  Enantiodivergent Synthesis and One-Pot Entry of Dimethylamino Functionality in the Purine Rings
  作者：Atanu Roy、Kuheli Chakrabarty、Pradeep K. Dutta、Narayan C. Bar、Nupur Basu、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1021/jo981955r

  日期：1999.4.1

  Cyclization of appropriately designed enose-nitrones derived from D-glucose, having nitrone at C-5 or C-l and allylic/homoallylic functionalities at C-3 of the sugar backbone, afforded polyhydroxylated aminocarbocycles which were subsequently used as the precursors for carbocyclic nucleoside analogues (11, 13, 16, 21, and 23). The enantiodirecting synthesis of both the enantiomeric pairs of nucleoside analogues 11 and 13, 21a and 23a, and 21c and 23c, has also been demonstrated by judiciously applying intramolecular nitrone cycloaddition (INC) reaction. An interesting observation was that in the cyclization reaction of pyrimidine ring to purine ring in DMF solvent, the substitution of C-6 chloro group with a dimethylamino functionality also occurred spontaneously under mild condition, though similar reactions are reported to occur at higher temperature. The hydrogen bonding between N-3 of the purine ring and an appropriate hydroxy substituent in the carbocycle seems to play a crucial role in this reaction.