allyl-α,β-L-arabinofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl-α,β-L-arabinofuranoside
• 英文别名: (3R,4R,5S)-2-(allyloxy)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；allyl-L-arabinofuranoside；(2S,3R,4R)-2-(hydroxymethyl)-5-prop-2-enoxyoxolane-3,4-diol
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: UYZLSMRCUXOHQO-QBARFFCXSA-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,β-L-arabinofuranoside 在 硫酸 、 potassium tert-butylate 、 sodium hydride 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 2,3,5-三-O-苄基-L-呋喃阿拉伯糖
  参考文献：
  名称：

  Convenient syntheses of 2,3,5-tri-O-benzyl-arabino- and −ribofuranoses via their allyl glycosides

  摘要：

  DOI：

  10.1016/0008-6215(91)80132-7
• 作为产物：
  描述：

  L-阿拉伯糖 、 烯丙醇 在 乙酰氯 作用下， 反应 15.0h， 以65%的产率得到allyl-α,β-L-arabinofuranoside
  参考文献：
  名称：

  Synthesis of the Spirastrellolide A, B/C Spiroketal: Enabling Solutions for Problematic Au(I)-Catalyzed Spiroketalizations

  摘要：

  A synthesis of the spirastrellolide A, B/C-ring monounsaturated spiroketal is reported. The key step relies on a Au-catalyzed spiroketalization of a propargyl triol employing an acetonide as a regioselectivity regulator. Through observation and analysis, a set of conditions has been developed that facilitates the use of a mixture of diastereomeric substrates, obviating the need to control the stereochemistry of the propargyl stereocenter and enabling a convenient retrosynthetic disconnection. The key reaction proceeds in 80% yield in 1 min at ambient temperature with the Me3PAuCl/AgOTf catalyst system. These conditions should be widely applicable for new synthetic endeavors as they appear to overcome all issues with the Au-catalyzed spiroketalization.

  DOI：

  10.1021/acs.orglett.5b00711

文献信息

• 2'-deoxy-L-nucleosides
  申请人：Watanabe Kyoichi

  公开号：US20050090660A1

  公开（公告）日：2005-04-28

  This invention provides processes for the preparation of compounds having the structure: wherein X and Y are same or different, and H, OH, OR, SH, SR, NH 2 , NHR′, or NR′R″ Z is H, F, Cl, Br, I, CN, or NH 2 . R is hydrogen, halogen, lower alkyl of C 1 -C 6 or aralkyl, NO 2 , NH 2 , NHR′, NR′R″, OH, OR, SH, SR, CN, CONH 2 , CSNH 2 , CO 2 H, CO 2 R′, CH 2 CO 2 H, CH 2 CO 2 R′, CH═CHR, CH 2 CH═CHR, or C═CR. R′ and R″ are same or different, and lower alkyl of C 1 -C 6 . R 13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate, or stabilized phosphate) or silyl; and

  这项发明提供了制备具有以下结构的化合物的方法： 其中 X和Y相同或不同，且H、OH、OR、SH、SR、NH2、NHR′或NR′R″ Z为H、F、Cl、Br、I、CN或NH2 R为氢、卤素、C1-C6的低碳烷基或芳基烷基、NO2、NH2、NHR′、NR′R″、OH、OR、SH、SR、CN、CONH2、CSNH2、CO2H、CO2R′、CH2CO2H、CH2CO2R′、CH═CHR、CH2CH═CHR或C═CR。 R′和R″相同或不同，且为C1-C6的低碳烷基。 R13为氢、烷基、酰基、磷酸酯（单磷酸酯、二磷酸酯、三磷酸酯或稳定磷酸酯）或硅基。
• Synthesis and in vitro synergistic antifungal activity of analogues of Panax stipulcanatus saponin against fluconazole-resistant Candida albicans
  作者：Shan Yin、Li Li、Liuqing Su、Hongfang Li、Yin Zhao、Yandan Wu、Ruina Liu、Fei Zou、Guanghui Ni

  DOI：10.1016/j.carres.2022.108575

  日期：2022.7

  Oleanolic acid 3-O-β-d-glucopyranosyl-(1 → 3)-β-d-glucopyranoside (1) and oleanolic acid 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-arabinofuranosyl-(1 → 4)]-β-d-glucopyranoside (2), novel Panax stipulcanatus saponin analogues, were synthesized for the first time starting from commercially available oleanolic acid, d-glucose, and L-(+)-arabinose. Glycosyl N-phenyltrifluoroacetimidates as donors and two-step

  齐墩果酸3 - O -β- d-吡喃葡萄糖基-(1→3)-β- d-吡喃葡萄糖苷( 1 )和齐墩果酸3 - O -β- d-吡喃葡萄糖基-(1→3)-[α - l-首次以市售齐墩果酸、d-葡萄糖和L-(+)-阿拉伯糖为原料合成了新的三七皂苷类似物阿拉伯呋喃糖基-(1→4)]-β- d-吡喃葡萄糖苷( 2 )。糖基N-苯基三氟乙酰亚胺酯作为供体和两步连续糖基化反应在合成中至关重要。体外抗真菌活性结果表明类似物2与氟康唑联用对耐氟康唑的白色念珠菌具有协同抗真菌活性，MIC 50值为31.80 μg/mL，FICI 值为0.32。我们还发现，中间体化合物16和17在与氟康唑联合使用时对敏感的白色念珠菌具有协同抗真菌活性，MIC 50值分别为 1.43 μg/mL 和 1.59 μg/mL，FICI 值分别为 0.29 和 0.32。
• Synthesis of 2'-deoxy-l-nucleosides
  申请人：Pharmasset Limited

  公开号：EP1600451A2

  公开（公告）日：2005-11-30

  The present invention provides a process for the preparation of a 2'-deoxy-L-nucleoside comprising the steps of: a) preparing a 2'-halo-L-nucleoside of the following formula:    wherein B is a heterocyclic or heteroaromatic base, R8 and R9 are independently hydrogen or a suitable protecting group, V is a halogen; and b) reducing the 2'-halo-L-nucleoside to a 2'-deoxy-L-nucleoside.

  本发明提供了一种制备 2'-脱氧-L-核苷的工艺，包括以下步骤： a) 制备下式的 2'-卤代-L-核苷： 其中 B 是杂环或杂芳族基团，R8 和 R9 独立地为氢或合适的保护基团，V 是卤素；以及 b) 将 2'-卤代-L-核苷还原成 2'-脱氧-L-核苷。
• Synthesis of 2'-deoxy-L-nucleosides
  申请人：Pharmasset Limited

  公开号：EP1600452A2

  公开（公告）日：2005-11-30

  The present invention provides a process for the preparation of a 2'-deoxy-L-nucleoside comprising the following steps: a) preparing from a suitably protected and activated L-furanose a 2-S-substituted-2-deoxy-L-furanose of the following formula: wherein B is a heterocyclic or heteroaromatic base, R8 and R9 are independently hydrogen or a suitable protecting group; R7 is a suitable protecting group; b) cyclizing the 2-S-substituted-2-deoxy-L-furanose to form a cyclonucleoside of the following formula: and c) reducing the cyclonucleoside to a 2'-deoxy-L-nucleoside.

  本发明提供了一种制备 2'-脱氧-L-核苷的工艺，包括以下步骤： a) 由适当保护和活化的 L-呋喃糖制备下式的 2-S-取代的-2-脱氧-L-呋喃糖： 其中 B 是杂环基或杂芳香基，R8 和 R9 独立地为氢或合适的保护基团；R7 是合适的保护基团； b) 环化 2-S-取代的-2-脱氧-L-呋喃糖，形成下式的环核苷： 和 c) 将环核苷还原成 2'-脱氧-L-核苷。
• FINCH, PAUL;ISKANDER, GEORGE M.;SIRIWARDENA, ALOYSIUS H., CARBOHYDR. RES., 210,(1991) C. 319-325
  作者：FINCH, PAUL、ISKANDER, GEORGE M.、SIRIWARDENA, ALOYSIUS H.

  DOI：——

  日期：——