methyl L-arabinoside | 449173-64-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl L-arabinoside
• 英文别名: Methyl l-arabinopyranoside；(3R,4S,5S)-2-methoxyoxane-3,4,5-triol
• CAS: 449173-64-2
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: ZBDGHWFPLXXWRD-NSHGFSBMSA-N

物化性质

• 沸点：
  314.0±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氧化氘、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  methyl L-arabinoside 在 盐酸 作用下， 以 水 为溶剂， 反应 30.0h， 生成 L-(+)-arabinose
  参考文献：
  名称：

  Saponin and sapogenol. XXXIX. Structure of soyasaponin A1, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max Merrill.

  摘要：

  从豆科植物大豆（Glycine max Merrill）的种子中分离出五种具有生物活性的三萜类低聚糖苷，分别命名为大豆皂苷I、II、III、A1（3）和A2（2）。通过采用两种选择性裂解方法，即光化学降解法和四乙酸铅降解法（这是四种可用于低聚糖苷中葡萄糖醛酸连接的选择性裂解方法中的两种），阐明了大豆皂苷A1的结构为：3-O[β-D-葡萄吡喃糖基（1→2）-β-D-半乳吡喃糖基（1→2）-β-D-葡萄糖醛吡喃糖基]-22-O[β-D-葡萄吡喃糖基（1→3）-α-L-阿拉伯吡喃糖基]-大豆皂苷元A（3）。

  DOI：

  10.1248/cpb.33.1069
• 作为产物：
  描述：

  hederagenin 23-O-α-arabinopyranoside (CP₀) 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 常春藤皂苷元 、 methyl L-arabinoside
  参考文献：
  名称：

  Kizu, Haruhisa; Tomimori, Tsuyoshi, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 9, p. 3340 - 3346

  摘要：

  DOI：

文献信息

• Saponin and sapogenol. XXXVIII. Structure of soyasaponin A2, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max Merrill.
  作者：ISAO KITAGAWA、MASAYUKI SAITO、TOSHIO TANIYAMA、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.33.598

  日期：——

  Two new bisdesmosides of soyasapogenol A (1), named soyasaponin A1 and soyasaponin A2 (7), were isolated from soybean, the seeds of Glycine max MERRILL, together with the known soyasaponins I (4), II (5), and III (6). By employing a photochemical degradation method, which is a selective cleavage method for the glucuronide linkage in oligoglycosides, and on the bases of spectral analyses and chemical reactions, the structure of soyasaponin A2 was elucidated as 3-O-[β-D-galactopyranosyl (1→2)-β-D-glucuronopyranosyl]-22-O-[β-D-glucopyranosyl (1→3)-α-L-arabinopyranosyl] soyasapogenol A (7).

  从大豆（Glycine max MERRILL的种子）中分离出两种新的大豆皂醇A（1）的双糖苷，命名为大豆皂苷A1和大豆皂苷A2（7），以及已知的大豆皂苷I（4）、II（5）和III（6）。通过采用光化学降解方法，这是一种针对寡糖苷中葡萄糖醛酸键的选择性断裂方法，并基于光谱分析和化学反应，确定了大豆皂苷A2的结构为3-O-[β-D-半乳糖吡喃糖基（1→2）-β-D-葡萄糖醛酸吡喃糖基]-22-O-[β-D-葡萄糖吡喃糖基（1→3）-α-L-阿拉伯糖吡喃糖基]大豆皂醇A（7）。
• 2-脱氧-L-核糖的制备方法
  申请人：何遂庆

  公开号：CN102153600B

  公开（公告）日：2016-09-14

  本发明涉及一种以L‑阿拉伯糖为原料制备2‑脱氧‑L‑核糖的方法，其由七个步骤组成，包括保护、基团活化、转化、脱保护和纯化步骤，合成反应条件普通，没有高温、高压、超真空，易控制，原料廉价易得，过程中有酸催化、有机碱催化、强酸性阳离子交换树脂、偶氮二异丁腈催化，用苯甲醛、苯甲酸还原，有机溶剂萃取，所用介质廉价易得，无毒，且收率高，成本低，适合工业化生产。
• Synthesis of beta-L-2'-deoxy nucleosides
  申请人：Storer Richard

  公开号：US20050059632A1

  公开（公告）日：2005-03-17

  An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro- 1 -furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

  提供了一种改进的2'-改性核苷和2'-脱氧核苷的制备工艺，例如，β-L-2'-脱氧胸苷（LdT）。特别是，改进的工艺针对的是2'-脱氧核苷的合成，该合成可能使用不同的起始材料，但都通过氯糖中间体或通过2,2'-脱水-1-呋喃糖核苷中间体进行。当使用2,2'-脱水-1-呋喃糖碱基中间体时，会采用还原剂（如Red-Al）和隔离剂（如15-冠-5醚），它们能引起分子内位移反应，并形成所需核苷产品的高收率。本发明的一种替代工艺使用2,2'-脱水-1-呋喃糖碱基中间体而不使用隔离剂，也能以高收率获得2'-脱氧核苷。根据本发明制成的化合物可以作为制备其他核苷类似物的中间体，或者可以直接用作抗病毒和/或抗肿瘤剂。
• 18-Norspirostanol derivatives from Trillium tschonoskii
  作者：Kimiko Nakano、Toshihiro Nohara、Toshiaki Tomimatsu、Toshio Kawasaki

  DOI：10.1016/0031-9422(83)85061-4

  日期：1983.1

  Abstract Three 18-norspironstanol oligoglycosides partly acylated in their sugar moieties were isolated from the underground parts of Trillium tschonoskii. Their structures were characterized, as 1-O-[2″,3″,4″-tri-O-acetyl-α- l -rhamnopyranosyl-(1 → 2)-α- l -arabinopyranosyl]-epitrillenogenin-24-O-acetate, 1-O-[2″,3″,4″-tri-O-acetyl-α- l -rhamno-pyranosyl-(1 → 2)-α- l -arabinopyranosyl]-epitrillenogenin

  摘要 从延龄草的地下部分中分离得到三个糖基部分酰化的18-去甲螺环甾烷醇寡糖苷。它们的结构被表征为 1-O-[2",3",4"-tri-O-乙酰基-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl]-epitrillenogenin-24-O -乙酸盐，1-O-[2″,3″,4″-三-O-乙酰基-α-l-鼠李糖-吡喃糖基-(1 → 2)-α-l-阿拉伯吡喃糖基]-表三甲萘醌和 1-O- [2",4"-di-O-乙酰基-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl]-epitrillenogenin-24-O-acetate。
• Immunostimulatory and Antitumor Activities of Monoglycosylceramides Having Various Sugar Moieties.
  作者：Kazuhiro MOTOKI、Masahiro MORITA、Eiichi KOBAYASHI、Takeshi UCHIDA、Kohji AKIMOTO、Hideaki FUKUSHIMA、Yasuhiko KOEZUKA

  DOI：10.1248/bpb.18.1487

  日期：——

  Ten kinds of monoglycosylceramides (MonoCers), having the same ceramide portion and different sugar moieties, were synthesized and their immunostimulatory and antitumor activities were examined. The manner of combination between sugar and ceramide has been demonstrated to affect the manifestation of immunostimulatory and resultant antitumor activities of MonoCers, and in the case of D-MonoCers having the D-sugar, α-D-MonoCers (sugar combined to ceramide in an α-configuration) show stronger activities than β-D-MonoCers. Furthermore, the form of sugar, not the furanose-form but the pyranose-form, and the 2''-and 4''-hydroxyl groups of the pyranose-form of sugar, seemed to play an important role in the manifestation of the activities of α-D-MonoCers.

  合成了十种单糖基神经酰胺（MonoCers），它们具有相同的神经酰胺部分和不同的糖基部分，并研究了它们的免疫刺激和抗肿瘤活性。糖与神经酰胺的结合方式已被证明会影响MonoCers的免疫刺激及其相应的抗肿瘤活性的表现。对于含有D-糖的D-MonoCers，α-D-MonoCers（糖以α-构型与神经酰胺结合）显示出比β-D-MonoCers更强的活性。此外，糖的形式，不是呋喃糖形式而是吡喃糖形式，以及吡喃糖形式的糖的2''和4''-羟基，似乎在α-D-MonoCers的活性表现中起着重要作用。