3-amino-5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose | 302582-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-amino-5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose
• 英文别名: (3aR,5S,6R,6aR)-6-amino-2,2-dimethyl-5-(phenylmethoxymethyl)-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-6-carbonitrile
• CAS: 302582-09-8
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: UIDWCXZLZJIWMG-HLPPOEQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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-5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 在 吡啶 、 potassium carbonate 、 caesium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 7.0h， 生成 (3R,3'aR,5'S,6'aR)-2-benzyl-2',2',5-trimethyl-1,1-dioxo-5'-(phenylmethoxymethyl)spiro[1,2-thiazole-3,6'-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole]-4-amine
  参考文献：
  名称：

  通过糖介导的糖基-α-磺酰胺基腈的分子内磺酰胺分子内环化反应（CSIC协议）在糖模板上合成4-氨基-5- H -2,3-二氢异噻唑-1,1-二氧化物环系

  摘要：

  使用碳酸钾，碳酸铯，n- BuLi和LDA作为碱已广泛研究了衍生自易得单糖的糖-α-磺酰胺基腈的碳负离子介导的磺酸盐分子内环化反应（CSIC方案）。结果，已经有效地制备了一系列对映体纯的螺（4-氨基-5- H -2，3-二氢异噻唑-1，1-二氧化物）衍生物，并以高收率分离。这些新的双环系统的合成是访问TSAO核苷（ATSAOs）的一系列氮杂类似物的关键。

  DOI：

  10.1021/jo035301g
• 作为产物：
  描述：

  5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose 在 titanium(IV) isopropylate 、 氨 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 3-amino-5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose
  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

• First Synthesis and Evaluation of the Inhibitory Effects of Aza Analogues of TSAO on HIV-1 Replication
  作者：Albert Nguyen Van Nhien、Cyrille Tomassi、Christophe Len、José Luis Marco-Contelles、Jan Balzarini、Christophe Pannecouque、Erik De Clercq、Denis Postel

  DOI：10.1021/jm050091g

  日期：2005.6.1

  Aza TSAO-T derivatives bearing a dihydroisothiazole dioxide ring instead of an oxathiole dioxide ring at the C-3 ' position on the sugar moiety were prepared. We have synthesized four families of compounds depending on substitution at both N-3 and N-2 ''. Biological evaluation showed that these compounds are HIV-1(IIIB)-specific and potent reverse transcriptase inhibitors with EC50 values between 0.13 and 3.5 mu M in cell culture.
• Synthesis and anti-HIV1 biological activity of novel 5″-ATSAO compounds
  作者：Cyrille Tomassi、Albert Nguyen Van Nhien、José Marco-Contelles、Jan Balzarini、Christophe Pannecouque、Erik De Clercq、Denis Postel

  DOI：10.1016/j.bmc.2008.02.026

  日期：2008.4

  Aza TSAO-T derivatives bearing a substituted dihydroisothiazole dioxide ring with a phenyl group at 500 position were repared. Biological evaluation showed that phenyl group gives rise to a dramatical decrease of the inhibitory effect. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.
• 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.
• Preparation of Spiro[4.4]oxaphospholene and -azaphospholene Systems from Carbohydrate Templates
  作者：Marina Moura、Solen Josse、Denis Postel

  DOI：10.1021/jo400954p

  日期：2013.9.20

  Introduction of a spiro-phosphorus cycle in position 3 of monosaccharidic derivatives was studied starting from cyanohydrin or aminonitrile A. A two-step procedure involving (i) phosphonylation and (ii) carbanion-mediated phosphonate intramolecular cyclization (denoted CPIC) was used. The necessity of having an electron-withdrawing group alpha to the phosphorus atom in order to avoid undesired reactions was demonstrated.