3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose | 52340-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
• 英文别名: 1,2:5,6-di-O-isopropylidene-3-deoxy-3-amino-3-cyano-α-D-glucofuranose；(3aR,5S,6R,6aR)-6-amino-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-6-carbonitrile
• CAS: 52340-61-1
• 化学式: C₁₃H₂₀N₂O₅
• 分子量: 284.312
• InChiKey: GRMDNYOSJNASRU-OAZVDXGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 在 sodium hydroxide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 6.0h， 生成 1,2:5,6-di-O-isopropylidenespiro[3-deoxy-α-D-ribohexofuranose-3,5'-imidazolidine]-2',4'-dione
  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：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 titanium(IV) isopropylate 、 氨 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 3-amino-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
  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。
• Stereocontrolled synthesis of (5+5), (5+6) and (6+6) 3-spiropseudonucleosides
  作者：Consolación Gasch、José M. Illangua、Penélope Merino-Montiel、José Fuentes

  DOI：10.1016/j.tet.2009.03.038

  日期：2009.5

  3-Spiropseudonucleosides, in which the heterocyclic base is a five-membered (oxazolidine, imidazolidine, thiohydantoin) or six-membered (perhydrooxazine) heterocycle, have been prepared starting from a hexofuranos-3-ulose. The method leads to good yields and is completely stereoselective. The key intermediate is a sugar iso(thio)cyanate.

  已经从六呋喃糖-3-基糖开始制备了3-螺伪假核苷，其中杂环碱基是五元（恶唑烷，咪唑烷，硫代乙内酰脲）或六元（全氢恶嗪）杂环。该方法产生了良好的产率，并且是完全立体选择性的。关键中间体是糖异（硫）氰酸酯。
• Nascent-HBr-Catalyzed Removal of Orthogonal Protecting Groups in Aqueous Surfactants
  作者：Shilpi Gupta、Smritilekha Bera、Dhananjoy Mondal

  DOI：10.1021/acs.joc.9b02561

  日期：2020.2.21

  the hydrophobic core of the confined micellar medium in aqueous surfactant is described for the first time. The sustained-release nascent-HBr enabled the chemoselective cleavages of acid-sensitive orthogonal functionalities present in carbohydrates, amino alcohols, and hydroxylated acyclic compounds in good to excellent yields.

  在水环境中的有机反应最近已成为有前途的研究领域。首次描述了由分散的催化剂苄基溴的缓慢水解生成的新生HBr，其中内部水存在于含水表面活性剂中的受限胶束介质的疏水核中。持续释放的新生HBr能够以良好或极好的收率对碳水化合物，氨基醇和羟基化无环化合物中存在的酸敏感性正交官能团进行化学选择性切割。
• Synthesis of conformationally rigid sugar-fused lactones and sugar α-amino acids
  作者：Shilpi Gupta、Smritilekha Bera、Dhananjoy Mondal

  DOI：10.1016/j.tet.2023.133646

  日期：2023.10

  The synthesis of conformationally constrained non-anomeric furanoid sugar quaternary α-amino acids and sugar-fused δ- and γ-lactones from d-glucose have been accomplished. The furanoid sugar α-amino acids were accessed via generation of the quaternary centre at the C-3 position of glucose with the installation of amine and nitrile functionality producing the aminonitrile derivative as a single diastereomer

  由d-葡萄糖合成构象受限的非异头呋喃糖季α-氨基酸和糖融合的δ-和γ-内酯。通过在葡萄糖的 C-3 位上生成四级中心并安装胺和腈官能团，产生作为单一非对映异构体的氨基腈衍生物，从而获得呋喃类糖 α-氨基酸。氨基腈衍生物的 C-6 伯羟基的Pinner 环化为葡萄糖稠合 δ-内酯的形成铺平了道路。这些糖内酯的碱性水解和其他后续反应产生糖融合的γ-内酯和糖模板天冬氨酸、酮官能化谷氨酸和高丝氨酸。
• 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.