(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(benzooxazol-2-ylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 848915-00-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(benzooxazol-2-ylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(1,3-benzoxazol-2-ylsulfanyl)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 848915-00-4
• 化学式: C₂₇H₃₂N₂O₁₃S
• 分子量: 624.623
• InChiKey: GCUTXQDFTXQBJR-WMDHSACJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  221
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(benzooxazol-2-ylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 methyl (4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-3-hydroxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Thiomidoyl approach to the synthesis of α-sialosides

  摘要：

  Novel sialosyl donors, S-benzoxazolyl (SBox) and S-thiazolyl (STaz) sialosides, have been synthesized and applied to the stereoselective synthesis of alpha-sialosides. It was also demonstrated that it is possible to selectively activate SBox sialyl donor over ethyl thioglycoside, allowing the direct synthesis of disaccharide donors that could be used in subsequent glycosylations without further manipulations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.043
• 作为产物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 、 potassium 2-mercaptobenzoxazolate 在 18-冠醚-6 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以80%的产率得到(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(benzooxazol-2-ylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Thiomidoyl approach to the synthesis of α-sialosides

  摘要：

  Novel sialosyl donors, S-benzoxazolyl (SBox) and S-thiazolyl (STaz) sialosides, have been synthesized and applied to the stereoselective synthesis of alpha-sialosides. It was also demonstrated that it is possible to selectively activate SBox sialyl donor over ethyl thioglycoside, allowing the direct synthesis of disaccharide donors that could be used in subsequent glycosylations without further manipulations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.043

文献信息

• Solvent Effect in the Synthesis of Sialosyl α(2-6) Galactosides: Is Acetonitrile the only Choice?
  作者：Cristina De Meo、Michael Farris、Nathan Ginder、Bonnie Gulley、Uvege Priyadarshani、Matthew Woods

  DOI：10.1002/ejoc.200800278

  日期：2008.7

  In spite of notable achievements for the synthesis of α-sialosides that have been made in the past decades, sialylation reactions often require low temperatures (–40 to –78 °C) and the use of acetonitrile as a solvent. Herein we report that a C-5 oxazolidinone sialosyl donor gives high yields andstereoselectivities in the presence of dichloromethane and/or tetrahydrofuran at 0 °C. Surprisingly, high

  尽管过去几十年在合成 α-唾液酸苷方面取得了显著成就，但唾液酸化反应通常需要低温（–40 至 –78 °C）并使用乙腈作为溶剂。在本文中，我们报告了 C-5 恶唑烷酮唾液酸供体在二氯甲烷和/或四氢呋喃存在下在 0°C 下具有高产率和立体选择性。令人惊讶的是，即使在环境温度下，在四氢呋喃中也能获得高立体选择性和产率。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008）
• METHOD FOR PREPARING HEXOSE DERIVATIVES
  申请人：Hung Shang Cheng

  公开号：US20090105466A1

  公开（公告）日：2009-04-23

  A method for preparing hexose derivatives comprises the steps of providing a silylated hexose, treating the silylated hexose with a first carbonyl compound in the presence of a catalyst to form an ketalized hexose, treating the ketalized hexose with a second carbonyl compound followed by treating with a first reductant to form an etherized hexose, and converting the etherized hexose into a target hexose derivative, which can be 2-alcohol hexose, 3-alcohol hexose, 4-alcohol hexose, or a 6-alcohol hexose. In particular, the present invention can prepare the hexose derivatives with highly regioselective scheme to protect individual hydroxyls of monosaccharide units and install an orthogonal protecting group pattern in a one-pot manner

  制备己糖衍生物的方法包括以下步骤：提供硅烷基化的己糖，将硅烷基化的己糖与第一羰基化合物在催化剂存在下处理，形成缩酮化的己糖，将缩酮化的己糖与第二羰基化合物处理后，再用第一还原剂处理，形成醚化的己糖，并将醚化的己糖转化为目标己糖衍生物，可以是2-醇己糖、3-醇己糖、4-醇己糖或6-醇己糖。具体来说，本发明可以采用高度选择性的方案制备己糖衍生物，以保护单糖单元的各个羟基，并以一锅法安装正交保护基图案。