methyl 2,3,4-tri-O-methyl-L-rhamnopyranoside | 14200-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-methyl-L-rhamnopyranoside
• 英文别名: methyl 2,3,4-tri-O-methylrhamnopyranoside；(3R,4R,5S,6S)-2,3,4,5-tetramethoxy-6-methyloxane
• CAS: 14200-00-1
• 化学式: C₁₀H₂₀O₅
• 分子量: 220.266
• InChiKey: FHJGOJSYFDDBAA-HQRRAASTSA-N

物化性质

• 沸点：
  90-93 °C(Press: 0.2 Torr)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-methyl-L-rhamnopyranoside 在 盐酸 、 水 作用下， 反应 5.0h， 生成 (3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-ol
  参考文献：
  名称：

  PESTICIDAL COMPOSITIONS

  摘要：

  本文件揭示的发明涉及杀虫剂领域及其在控制害虫方面的应用。公开了具有以下结构的化合物。

  公开号：

  US20100204164A1
• 作为产物：
  描述：

  methyl (11S)-11-[(2R,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6S)-3-hydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxyhexadecanoate 生成 methyl 2,3,4-tri-O-methyl-L-rhamnopyranoside
  参考文献：
  名称：

  KITAGAWA, ISAO;BAEK, NAM IN;OHASHI, KAZUYOSHI;SAKAGAMI, MASAHIRO;YOSHIKAW+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1131-1133

  摘要：

  DOI：

文献信息

• Legume saponin of Gleditsia japonica Miquel. II. Desmonoterpenyl glycoside of echinocystic acid.
  作者：TAKAO KONOSHIMA、HIDEO INUI、KEIKO SATO、MARI YONEZAWA、TOKUNOSUKE SAWADA

  DOI：10.1248/cpb.28.3473

  日期：——

  Three triterpenoid saponins were isolated from legumes of Gleditsia japonica cv.'Saponifera'(Leguminosae). These saponins are rare examples of triterpenoid saponins containing monoterpenes. The desmonoterpenyl compound, C74H120O38, [α]23D -42.3°(MeOH), which was obtained from them by alkali hydrolysis with K2CO3, was characterized as a 3, 28-O-bisglycoside on the basis of physical data and degradation products.

  从日本菱角树（Leguminosae）品种"Saponifera"的豆荚中分离出了三种三萜皂苷。这些皂苷是含有单萜的三萜皂苷的稀有例子。通过与K2CO3进行碱性水解，从中获得的去单萜基化合物C74H120O38， [α]23D -42.3°（MeOH），根据物理数据和降解产物的特征，被鉴定为3, 28-O-双糖苷。
• Saponin and sapogenol. XXXIII. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (3). Azukisaponins V and VI.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI SAITO、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.683

  日期：——

  The chemical structures of azukisaponins V (1) and VI (5), two of the six oligoglycosidic ingredients of total azukisaponin isolated from azuki beans, the seeds of Vigna angularis (WILLD.) OHWI et OHASHI (Leguminosae), were investigated. By means of photochemical degradation and chemical analyses, the structures of azukisaponins V and VI were elucidated to be 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl]-soyasapogenol B (1) and 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl]-29-O-[β-D-glucopyranosyl (1→6)-β-D-glucuronopyranosyl] azukisapogenol (5), respectively. Azukisaponin VI (5) is the first reported example of a 3, 29-bisdesmoside of an oleanene oligoglycoside.

  研究了从红豆（Vigna angularis (WILLD.) OHWI et OHASHI）中提取的总红豆皂苷的六种寡糖苷成分中的两种：红豆皂苷V（1）和VI（5）的化学结构。通过光化学降解和化学分析，阐明了红豆皂苷V和VI的结构分别为3-O-[α-L-鼠李糖吡喃基（1→2）-β-D-葡萄糖吡喃基（1→2）-β-D-葡萄糖醛酸吡喃基]-大豆皂苷醇B（1）和3-O-[β-D-葡萄糖吡喃基（1→2）-β-D-葡萄糖醛酸吡喃基]-29-O-[β-D-葡萄糖吡喃基（1→6）-β-D-葡萄糖醛酸吡喃基]红豆皂苷醇（5）。红豆皂苷VI（5）是首次报道的三、二十九双配糖体的鞘脂寡糖苷。
• Saponin and sapogenol. XL. Structure of sophoraflavoside I, a bisdesmoside of soyasapogenol B, from Sophorae Radix, the root of Sophora flavescens Aiton.
  作者：MASAYUKI YOSHIKAWA、HUIKANG WANG、HIROSHI KAYAKIRI、TOSHIO TANIYAMA、ISAO KITAGAWA

  DOI：10.1248/cpb.33.4267

  日期：——

  A new bisdesmoside of soyasapogenol B (3), named sophoraflavoside I (2), was isolated together with soyasaponin I (1) from Sophorae Radix (Sophora flavescens AITON, root). By employing a photochemical cleavage method for the glucuronide linkage in 2 and on the bases of chemical reactions and spectral analyses, the structure of sophoraflavoside I has been determined to be 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucuronopyranosyl]-22-O-[β-D-glucopyranosyl (1→2)-α-L-arabinopyranosyl] soyasapogenol B (2).

  一种新的大豆皂苷B的双脱糖苷（3），命名为黄豆黄酮苷I（2），与大豆皂苷I（1）从菟丝子根（Sophora flavescens AITON，根）中分离出来。通过采用光化学裂解法处理2中的葡萄糖醛酸连接基，并基于化学反应和光谱分析，确定黄豆黄酮苷I的结构为3-O-[α-L-甘露糖吡喃糖（1→2）-β-D-半乳糖吡喃糖（1→2）-β-D-葡萄糖醛酸吡喃糖]-22-O-[β-D-葡萄糖吡喃糖（1→2）-α-L-阿拉伯吡喃糖] 大豆皂苷B（2）。
• Saponin and sapogenol. XXXVII. Chemical constituents of astragali radix, the root of Astragalus membranaceus Bunge. (4). Astragalosides VII and VIII.
  作者：ISAO KITAGAWA、HUIKANG WANG、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.31.716

  日期：——

  By means of enzymatic degradation and by application of a selective cleavage method for the glucuronide linkage, as well as by the carbon-13 nuclear magnetic resonance (13C-NMR) analysis, the structures of two astragalosides, which were isolated as two of eleven astragalosidesfrom Astragali Radix (the root of Korean Astragalus membranaceus, Leguminosae), were elucidated : astragaloside VII is 3-O-β-D-xylopyranosyl-6-O-β-D-glucopyranosyl-25-O-β-D-glucopyranosyl-cycloastragenol (4) and astragaloside VIII is 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-xylopyranosyl (1→2)-β-D-glucuronopyranosyl] soyasap-ogenl B (8). Astragaloside VII (4) is an unprecedented example of a triterpene-tridesmoside.

  通过酶降解以及针对葡萄糖苷连接的选择性裂解方法结合碳-13核磁共振（13C-NMR）分析，阐明了从黄芪根（韩国黄芪，豆科植物）中分离出的两种黄芪苷的结构，这两种黄芪苷是十一种黄芪苷中的两种：黄芪苷VII为3-O-β-D-木糖吡喃糖基-6-O-β-D-葡萄糖吡喃糖基-25-O-β-D-葡萄糖吡喃糖基-环黄芪醇（4），黄芪苷VIII为3-O-[α-L-鼠李吡喃糖（1→2）-β-D-木糖吡喃糖（1→2）-β-D-葡萄糖醛酸吡喃糖]大豆皂苷B（8）。黄芪苷VII（4）是一个前所未有的三萜-三糖苷的例子。
• Studies on Catalytic Enantioselective Total Synthesis of Caprazamycin B: Construction of the Western Zone
  作者：Purushothaman Gopinath、Takumi Watanabe、Masakatsu Shibasaki

  DOI：10.1021/jo301803h

  日期：2012.10.19

  catalyst furnished the β-hydroxy thioamide in good yield and enantioselectivity. On further transformation, the thioamide functionality was converted to the corresponding β-hydroxy ester. Finally, a convergent synthesis of the western zone of caprazamycin B was achieved by connecting the hemiester, the β-hydroxy ester, and the 2,3,4-tri-O-methyl-l-rhamnose fragments.

  我们描述了使用两个催化不对称反应作为我们方法的关键要素的一种简单便捷的卡普沙霉素B西部区域的合成方法。以（S）-Ni 2-（席夫碱）络合物为催化剂对3-甲基戊二酸酐进行不对称化反应，得到了手性半酯，以及与间苯二酚，（R，R）-Ph-BPE和2的硫酰胺-醛醇缩合反应， 2,5,7,8-五甲基苯并二氢苯并二氢苯并二氢吡喃醇作为催化剂以良好的产率和对映选择性提供了β-羟基硫代酰胺。进一步转化后，将硫酰胺官能团转化为相应的β-羟基酯。最后，通过连接半酯，β-羟基酯和2,3,4-tri-O-甲基-1-鼠李糖片段。