3,4-di-O-acetyl-6-O-methylsulfonyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol | 103082-74-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 3,4-di-O-acetyl-6-O-methylsulfonyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol
• 英文别名: 3,4-tri-O-acetyl-6-O-mesyl-D-glucal；3,4-di-O-acetyl-6-O-mesyl-D-glucal；3,4-di-O-acetyl-6-O-methanesulfonyl-D-glucal；[(2R,3S,4R)-3-acetyloxy-2-(methylsulfonyloxymethyl)-3,4-dihydro-2H-pyran-4-yl] acetate
• CAS: 103082-74-2
• 化学式: C₁₁H₁₆O₈S
• 分子量: 308.309
• InChiKey: SKKYZJAMVYQTFG-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-6-O-methylsulfonyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol 在 三正丁基氢锡 、 lithium iodide 作用下， 以 甲苯 、 丁酮 为溶剂， 反应 137.0h， 生成 3,4-di-O-acetyl-D-rhamnal
  参考文献：
  名称：

  A Straightforward Access to 5-Deoxy-D-arabinono-1,4-lactone, a Versatile Intermediate in the Lauraceae Lactones Syntheses

  摘要：

  5-Deoxy-d-arabinono-1,4-lactone (2) 是通过 RuO4 催化氧化裂解 6-deoxyglucal diacetate (5d) 合成的，6-deoxyglucal diacetate 来自 d-glucal triacetate (3)，然后进行碱性水解和酸性处理。

  DOI：

  10.1246/bcsj.58.3629
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 吡啶 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 42.5h， 生成 3,4-di-O-acetyl-6-O-methylsulfonyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol
  参考文献：
  名称：

  A Straightforward Access to 5-Deoxy-D-arabinono-1,4-lactone, a Versatile Intermediate in the Lauraceae Lactones Syntheses

  摘要：

  5-Deoxy-d-arabinono-1,4-lactone (2) 是通过 RuO4 催化氧化裂解 6-deoxyglucal diacetate (5d) 合成的，6-deoxyglucal diacetate 来自 d-glucal triacetate (3)，然后进行碱性水解和酸性处理。

  DOI：

  10.1246/bcsj.58.3629

文献信息

• A simple and convenient method for the synthesis of pyranoid glycals
  作者：Jinzhong Zhao、Shanqiao Wei、Xiaofeng Ma、Huawu Shao

  DOI：10.1016/j.carres.2009.10.003

  日期：2010.1

  A simple, mild, and environmentally benign synthesis procedure of pyranoid glycals is described. In a novel fashion, protected glycopyranosyl bromides undergo the reductive elimination in the presence of zinc in phosphate buffer at room temperature. The pyranoid glycals were obtained in good-to-excellent yields (18 examples).

  描述了一种简单，温和的，对环境有益的吡喃糖类合成方法。以新颖的方式，在室温下在磷酸盐缓冲液中存在锌的情况下，受保护的吡喃葡萄糖基溴化物经历了还原消除。以良好至优异的产率获得了吡喃类糖（18个实施例）。
• An efficient method for the synthesis of pyranoid glycals
  作者：Heshan Chen、Ting Xian、Wan Zhang、Wenshuai Si、Xiaosheng Luo、Bo Zhang、Meiyu Zhang、Zhongfu Wang、Jianbo Zhang

  DOI：10.1016/j.carres.2016.05.013

  日期：2016.8

  A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30-60 °C. The corresponding glycals were obtained with excellent isolated yields (72-96%) in a short time (20-50 min). Furthermore, the transformation was

  设计了一种简单有效的方法来制备吡喃类糖。在30-60°C的条件下，在CH3CN中存在锌粉和氯化铵的情况下，以一系列新颖的方式对一系列受保护的吡喃葡萄糖基溴化物进行了还原消除。在短时间内（20-50分钟）以优异的分离产率（72-96％）获得了相应的糖。此外，该转化与不同的保护模式兼容且可方便地扩展（45 g乙酰溴葡萄糖为86％），使其非常适用于有机合成。
• A mild and environmentally benign method for the synthesis of glycals in PEG-600/H2O
  作者：Jinzhong Zhao、Shanqiao Wei、Xiaofeng Ma、Huawu Shao

  DOI：10.1039/b821681a

  日期：——

  Glycals were synthesized via a simple, mild, convenient and environmentally benign procedure, in which protected glycosyl bromides undergo the reductive elimination in the presence of zinc in PEG-600/H2O at room temperature. The glycals were obtained in 75–92% isolated yields.

  糖醇通过一种简单、温和、方便且环保的程序合成，在该过程中，保护的糖苷溴化物在室温下与锌在PEG-600/H2O的存在下进行还原消除反应。糖醇的分离产率为75-92%。
• A Rapid Synthesis of Pyranoid Glycals Promoted by β-Cyclodextrin and Ultrasound
  作者：Jinzhong Zhao、Huawu Shao、Xin Wu、Shaojing Shi

  DOI：10.1002/cjoc.201180263

  日期：2011.7

  procedure for the synthesis of glycals from glycosyl bromides with very low zinc dust loading (1.5 equiv.) is described. The process is activated by β‐cyclodextrin and ultrasound. Based on 19 samples, this method has been demonstrated to be highly effective for a broad range of glycosyl bromides, including acid‐ or base‐sensitive and disaccharide glycosyl bromides. A yield of 85%–96% of glycals was obtained

  描述了一种从糖基溴化物中合成锌粉的负荷非常低（1.5当量）的便捷且环境友好的方法。β-环糊精和超声波可激活该过程。基于19个样品，该方法已被证明对多种糖基溴化物都非常有效，包括对酸或碱敏感的二糖基糖基溴化物。获得了85％–96％的缩醛收率。
• C-Glycosylanthraquinone synthesis: total synthesis of vineomycinone B2 methyl ester
  作者：Marcus A. Tius、Jorge Gomez-Galeno、Xue Qin Gu、Javid H. Zaidi

  DOI：10.1021/ja00015a035

  日期：1991.7

  A synthesis of substituted anthraquinones has been developed. Commercially available anthrarufin and 1,8-dihydroxyanthraquinone were converted to the corresponding (methoxymethoxy)anthracenes. Directed metalation followed by stannylation produced stable intermediates that were either alkylated, arylated, acylated, and/or C-glycosylated. The value of this new methodology was demonstrated by the triply convergent total synthesis of vineomycinone B2 methyl ester, a representative C-glycosylanthraquinone antibiotic.