allyl α-L-arabinofuranoside | 134149-34-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl α-L-arabinofuranoside
• 英文别名: allyl-α-L-arabinofuranoside；(2S,3R,4R,5R)-2-(hydroxymethyl)-5-prop-2-enoxyoxolane-3,4-diol
• CAS: 134149-34-1
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: UYZLSMRCUXOHQO-RULNZFCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl α-L-arabinofuranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranoside
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of 1 → 5-Linked α-l-Arabinofuranosyl Oligosaccharides

  摘要：

  以阿拉伯呋喃糖基三氯乙酰亚氨酸酯为糖基供体，以未保护或部分保护的糖苷为受体，描述了呋喃糖基寡糖的区域和立体选择性合成，产率中等至非常好。介绍了 1 → 5 连接的δ-±-阿拉伯呋喃糖基八聚体的聚合合成。

  DOI：

  10.1055/s-1999-3170
• 作为产物：
  描述：

  L-阿拉伯糖 在 吡啶 、 sodium hydroxide 、 α-L-arabinofuranosidase (EC 3.2.1.55) 、 硫酸 、 ethanol; compound with boron fluoride 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 生成 allyl α-L-arabinofuranoside
  参考文献：
  名称：

  Enzymatic synthesis of alkyl arabinofuranosides using a thermostable α-l-arabinofuranosidase

  摘要：

  A thermostable alpha-L-arabinofuranosidase was tested for its ability to perform transglycosylation with different alcohol acceptors. Reactions were characterized by high rates with optimal synthesis being obtained within 10 min. Both primary and secondary alcohols could act as acceptors in transarabinosylation but yields of alkyl arabinosides decreased with increasing alkyl chain length. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02381-x

文献信息

• Araf51 with improved transglycosylation activities: one engineered biocatalyst for one specific acceptor
  作者：Alizé Pennec、Richard Daniellou、Pascal Loyer、Caroline Nugier-Chauvin、Vincent Ferrières

  DOI：10.1016/j.carres.2014.10.031

  日期：2015.1

  were selected on their ability to catalyze the transglycosylation reaction of p-nitrophenyl α-L-arabinofuranoside (pNP-Araf) used as a donor and various aliphatic alcohols as acceptors. This screening strategy underlined 5 interesting clones, each one corresponding to one acceptor. They appeared to be much more efficient in the transglycosylation reaction compared to the wild type enzyme whereas no self-condensation

  为了获得用于合成烷基阿拉伯呋喃糖苷的有效生物催化剂，已经进行了阿拉伯呋喃呋喃糖基水解酶Araf51的随机诱变。选择突变体是基于其催化用作供体的对硝基苯基α-L-阿拉伯呋喃糖苷（pNP-Araf）和各种脂族醇作为受体的转糖基化反应的能力。这种筛选策略强调了5个有趣的克隆，每个克隆对应一个受体。与野生型酶相比，它们在转糖基化反应中似乎更有效，而未检测到自缩合或水解产物。此外，突变体对已为其选择了醇的高特异性证实了筛选过程。突变酶的序列分析表明，
• Analysis of Configuration and Conformation of Furanose Ring in Carbohydrate and Nucleoside by Vibrational Circular Dichroism
  作者：Tohru Taniguchi、Kie Nakano、Ryosuke Baba、Kenji Monde

  DOI：10.1021/acs.orglett.6b03626

  日期：2017.1.20

  A reliable and convenient method for determining the configuration and conformation of the furanose ring in carbohydrates and nucleosides by vibrational circular dichroism (VCD) spectroscopy is described. Diastereomeric pairs of several furanose monosaccharides and nucleosides were prepared, and their VCD spectra were analyzed. The results revealed that VCD spectroscopy elucidates the equibrated state

  描述了一种可靠方便的方法，通过振动圆二色性（VCD）光谱确定碳水化合物和核苷中呋喃糖环的构型和构象。制备了几种呋喃糖单糖和核苷的非对映异构体对，并分析了它们的VCD光谱。结果表明，VCD光谱可阐明呋喃糖环折叠的平衡状态，而这通常很难通过其他技术进行研究。
• An efficient and concise regioselective synthesis of α-(1→5)-linked l-arabinofuranosyl oligosaccharides
  作者：Yuguo Du、Qingfeng Pan、Fanzuo Kong

  DOI：10.1016/s0008-6215(00)00159-2

  日期：2000.10

  A series of alpha-(1 --> 5)-linked L-arabinofuranosyl di-, tetra-, hexa- and octameric derivatives were synthesized efficiently. The process was carried out in a regio- and stereoselective manner using perbenzoylated arabinofuranosyl trichloroacetimidates as glycosyl donors and unprotected or partially protected arabinofuranosides as glycosyl acceptors in the presence of a catalytic amount of trimethylsilyl

  有效地合成了一系列由α-（1-> 5）连接的L-阿拉伯呋喃糖基二，四，六和八聚体衍生物。在催化量的三甲基甲硅烷基三氟甲磺酸盐（TMSOTf）存在下，使用过苯甲酰化的阿拉伯呋喃糖基三氯乙酰亚氨酸酯作为糖基供体，以未保护的或部分保护的阿拉伯呋喃糖苷作为糖基受体，以区域选择性和立体选择性的方式进行。
• Silver Triflate. A Mild Alternative Catalyst for Glycosylation Conditions Using Trichloroacetimidates as Glycosyl Donors
  作者：Guohua Wei、Guofeng Gu、Yuguo Du

  DOI：10.1081/car-120025325

  日期：2003.1.10

  Although trimethylsilyl triflate (TMSOTf) has been widely used to promote glycosyl trichloroacetimidates in oligosaccharide synthesis, silver triflate (AgOTf) was proved to be a mild and in some cases more efficient catalyst in TMSOTf-sensitive glycosylations. Migration and degradation in some specific coupling reactions can be reduced significantly under this alternative glycosylation condition.
• Regio- and Stereoselective Synthesis of 1 → 5-Linked α-l-Arabinofuranosyl Oligosaccharides
  作者：Yuguo Du、Qingfeng Pan、Fanzuo Kong

  DOI：10.1055/s-1999-3170

  日期：——

  Regio- and stereoselective synthesis of furanosyl oligosaccharides in moderate to very good yields using arabinofuranosyl trichloroacetimidates as glycosyl donors and unprotected or partially protected glycosides as acceptors was described. A convergent synthesis of 1 → 5-linked α-l-arabinofuranosyl octamer was presented.

  以阿拉伯呋喃糖基三氯乙酰亚氨酸酯为糖基供体，以未保护或部分保护的糖苷为受体，描述了呋喃糖基寡糖的区域和立体选择性合成，产率中等至非常好。介绍了 1 → 5 连接的δ-±-阿拉伯呋喃糖基八聚体的聚合合成。