3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose | 302582-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: 3-amino-3-C-cyano-3-deoxy-1,2-O-isopropylidene-5-O-trityl-α-D-ribofuranose；(3aR,5S,6R,6aR)-6-amino-2,2-dimethyl-5-(trityloxymethyl)-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-6-carbonitrile
• CAS: 302582-03-2
• 化学式: C₂₈H₂₈N₂O₄
• 分子量: 456.541
• InChiKey: FUBXSPSDRSMIKR-SPGPFUFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose 在 sodium hydroxide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 生成 (3R)-3,3-(1,3-diazaspiro-2,4-dioxo)-5-O-trityl-1,2-O-isopropylidene-α-D-ribofuranose
  参考文献：
  名称：

  D-核糖的螺乙内酰脲作为新的有效酶抑制剂。

  摘要：

  来自单糖的端粒螺乙内酰脲衍生物具有多种生物学特性。我们在本文中描述了D-阿洛糖和D-核糖的3-螺乙胆苷衍生物的合成。关键步骤是使用四异丙氧基钛作为温和有效的催化剂，由D-葡萄糖和D-木糖的蔗糖衍生物形成立体选择性的糖-α-氨基腈。从这些中间体合成了目标化合物。在酸性条件下，该糖部分被部分或完全脱保护。这些新的杂环单糖衍生物是有效的糖原磷酸化酶抑制剂。

  DOI：

  10.1211/0022357011776342
• 作为产物：
  描述：

  1,2-O-ISOPROPYLIDENE-5-O-(TRIPHENYLMETHYL)-伪-D-ERYTHRO-PENTOFURANOS-3-ULOSE 在 titanium(IV) isopropylate 、 氨 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 3-amino-3-C-cyano-3-deoxy-5-O-trityl-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Stereoselective synthesis of α-aminonitriles at non-anomeric positions of monosaccharides

  摘要：

  alpha-Aminonitriles have been stereoselectively introduced at non-anomeric positions of monosaccharides, in which the carbon C-alpha is one of the atoms of the sugar ring. Target compounds were prepared from various ulose derivatives and amines using titanium(IV) isopropoxide as a mild and effective Lewis acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01090-x

文献信息

• Synthesis and transformations of [1,2-O-isopropylidene-α-d-erythro (and α-d-ribo)furanose]-3-spiro-3′-(4′-amino-5′H-2′,3′-dihydroisothiazole-1′,1′-dioxide) derivatives
  作者：Albert Nguyen Van Nhien、Laura Domı́nguez、Cyrille Tomassi、M Rosario Torres、Christophe Len、Denis Postel、José Marco-Contelles

  DOI：10.1016/j.tet.2004.03.063

  日期：2004.5

  protocols) of glyco-α-sulfonamidonitriles derived from readily available uloses 1A and 1B have been investigated using different bases (potassium carbonate, cesium carbonate, LDA and n-BuLi). As a result, a series of enantiomerically pure [1,2-O-isopropylidene-α-d-erythro (and α-d-ribo)furanose]-3-spiro-3′-(4′-amino-5′H-2′,3′-dihydroisothiazole-1′,1′-dioxide) derivatives have been prepared and isolated

  已经使用不同的碱（碳酸钾，碳酸铯，LDA和正丁基锂）研究了衍生自易得的uloses 1A和1B的糖-α-磺酰胺基腈的碳负离子介导的磺酰胺环化（CSIC协议）。结果，产生了一系列对映体纯的[1,2 - O-异亚丙基-α-二赤（和α-d-核糖）呋喃糖] -3-spiro-3'-（4'-amino- 5'H -2'，3'-二氢异噻唑-1'，1'-二氧化物）衍生物已经制备并以高收率分离。
• New glycosyl-α-aminotetrazole-based catalysts for highly enantioselective aldol reactions
  作者：Lucie Wynands、Sébastien Delacroix、Albert Nguyen Van Nhien、Elena Soriano、José Marco-Contelles、Denis Postel

  DOI：10.1016/j.tet.2013.04.043

  日期：2013.6

  Direct aldol reactions of acetone with aromatic aldehydes have been achieved in high yielding and enantioselective processes using glycosyl-alpha-aminotetrazoles as a new class of organocatalysts. Computational studies at DFT level have been performed to account for the experimental observations. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel spirohydantoins of d-allose and d-ribose derived from glyco-α-aminonitriles
  作者：Denis Postel、Albert Nguyen Van Nhien、Pierre Villa、Gino Ronco

  DOI：10.1016/s0040-4039(00)02294-2

  日期：2001.2

  The synthesis of 3-spirohydantoin derivatives of D-allose and D-ribose is reported. The key step is the stereoselective conversion of glyco-alpha -aminonitriles from ulose derivatives of D-glucose and D-xylose using titanium(IV) isopropoxide as a mild and efficient catalyst. Cyclisation of the glyco-alpha -aminonitriles give the target spirohydantoins. (C) 2001 Elsevier Science Ltd. All rights reserved.
• New 4-amino-5-H-2,3-dihydroisothiazole-1,1-dioxides from sugar α-aminonitriles using the CSIC reaction
  作者：Denis Postel、Albert Nguyen Van Nhien、Pierre Villa、Gino Ronco

  DOI：10.1016/s0040-4039(00)02013-x

  日期：2001.1

  4-Amino-5-H-2,3-dihydroisothiazole-1,1-dioxide ring was attached to a monosaccharide ring system by carbanion-mediated sulfonate intramolecular cyclisation (CSIC) of either secondary or tertiary aminonitrilesulfonamide carbohydrate derivatives using NaH, Cs2CO3, or BuLi as a base. These new bicyclic systems were used as glycone precursors of aza analogues of TSAO RT inhibitors. We report the first synthesis of an aza analogue of TSAO-m(3)T. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of α-aminonitriles at non-anomeric positions of monosaccharides
  作者：Denis Postel、Albert Nguyen Van Nhien、Michelle Pillon、Pierre Villa、Gino Ronco

  DOI：10.1016/s0040-4039(00)01090-x

  日期：2000.8

  alpha-Aminonitriles have been stereoselectively introduced at non-anomeric positions of monosaccharides, in which the carbon C-alpha is one of the atoms of the sugar ring. Target compounds were prepared from various ulose derivatives and amines using titanium(IV) isopropoxide as a mild and effective Lewis acid. (C) 2000 Elsevier Science Ltd. All rights reserved.