methyl 3-O-methyl-β-L-rhamnopyranoside | 108267-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-methyl-β-L-rhamnopyranoside
• 英文别名: methyl acofriose；methyl 3-O-methyl-α-rhamnopyranoside；(2S,3R,4R,5S,6S)-2,4-dimethoxy-6-methyloxane-3,5-diol
• CAS: 108267-98-7
• 化学式: C₈H₁₆O₅
• 分子量: 192.212
• InChiKey: FAFYNFILENICIV-TXXZRHAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-O-methyl-β-L-rhamnopyranoside 、 4-溴苯甲酰氯 在 吡啶 作用下， 反应 3.0h， 生成 4-bromobenzoate of acofriose methyl glycoside
  参考文献：
  名称：

  一种来自红根瘤菌菌株DSM 30149的新型荚膜多糖。

  摘要：

  根瘤菌（Rhizobium rubi）菌株DSM 30149是革兰氏阴性植物致病细菌，它产生具有以下重复单元的线性多糖：通过光谱和化学方法确定了这种新结构。它呈现出另一种红宝石菌报道的相似的亲脂性特征。这些与来自根瘤菌科的共生成员的荚膜多糖种类已知的特征相反，即高度阴离子聚合物。

  DOI：

  10.1016/j.carres.2008.04.024
• 作为产物：
  描述：

  碘甲烷 、 L-rhamnose hydrate 在 二正丁基氧化锡 、 cesium fluoride 作用下， 以 甲醇 、 甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以70%的产率得到(2S,3R,4R,5R,6S)-2-Methoxy-6-methyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products

  摘要：

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.018

文献信息

• Regioselective methylation of methyl glycopyranosides with diazomethane in the presence of transition-metal chlorides and of boric acid
  作者：Evgeny V. Evtushenko

  DOI：10.1016/s0008-6215(99)00044-0

  日期：1999.3

  Abstract Partial methylation of the methyl pyranosides of a number of pentoses, hexoses, 6-deoxyhexoses, methyl uronates and their methyl ethers with diazomethane in the presence of transition-metal chlorides and boric acid was studied. It was found for methyl glycosides of pentoses and 6-deoxyhexoses that tin(II), antimony(III), and titanium(IV) chlorides as well as boric acid promoted substitution

  摘要研究了在过渡金属氯化物和硼酸存在下，许多戊糖，己糖，6-脱氧己糖，尿酸甲酯及其甲基醚的甲基吡喃糖苷与重氮甲烷的部分甲基化。发现戊糖和6-脱氧己糖的甲基糖苷中锡（II），锑（III）和钛（IV）氯化物以及硼酸主要促进OH-3的取代，但被铈（III）和锌的取代（II）观察到盐主要取代了OH-2。在所有情况下，甲基β-1-鼠李糖吡喃糖苷的甲基化表现出较高的OH-2反应性。在氯化锡（II），锑（III）和铈（III）的存在下，己糖甲基糖苷的甲基化反应主要产生了3-甲基醚。不参与进一步络合的3-甲基醚 积聚高达50-80％的反应混合物（95％至100％的单甲醚馏分）。建议用于许多糖的方便的甲基醚的合成。
• Calicheamicins, a novel family of antitumor antibiotics. 4. Structure elucidation of calicheamicins .beta.1Br, .gamma.1Br, .alpha.2I, .alpha.3I, .beta.1I, .gamma.1I, and .delta.1I
  作者：May D. Lee、Theresa S. Dunne、Conway C. Chang、Marshall M. Siegel、George O. Morton、George A. Ellestad、William J. McGahren、Donald B. Borders

  DOI：10.1021/ja00029a030

  日期：1992.1

  The details of the structural assignment of the potent antitumor antibiotic, calicheamicin gamma-1I (6, C55H74IN3O21S4), is reported. Methanolysis studies on 6 and N-acetylcalicheamicin gamma-1I (8, C57H76IN3022S4) permitted the structural assignment of the glycosidic chain. Details of the spectral analysis supporting the assignments of the 3-O-methyl-alpha-L-rhamnopyranoside (D-ring) and the methyl 2,4-dideoxy-3-O-methyl-4-(N-acetyl-N-ethylamino)-a-L-xylopyranoside (E-ring) is reported. The structure of calicheamicinone (32, C18H17NO5S3), containing a bicyclo[7.3.1 ] tridec-9-ene-2,6-diyne system and a methyl trisulfide, was elucidated by a series of chemical degradation studies, which included an unexpected free radical cycloaromatization reaction. The presence of 4,6-dideoxy-4-(hydroxyamino)-beta-D-glucopyranoside (A-ring) and its N-O glycosidic linkage to the thio sugar (B-ring) was ascertained by X-ray crystallography of 24 (C36H40INO13S2), a degradation product of 6. The chemical structures of calicheamicins beta-1Br (1), gamma-1Br (2), alpha-2I (3), alpha-3I (4), beta-1I (5), and delta-1I (7) were assigned by correlating their H-1 and C-13 NMR data with that of calicheamicin gamma-1I. By tracking the biological activities of the degradation products, the enediyne system of calicheamicinone was shown to be essential for the DNA-damaging abilities of the calicheamicins. A mechanism whereby the enediyne could be triggered to cyclize via a 1,4-diyl, the putative DNA cleaving species, is proposed.