2-acetamido-2,3-dideoxy-α-D-erythro-hex-2-enofuranose | 58546-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-acetamido-2,3-dideoxy-α-D-erythro-hex-2-enofuranose
• 英文别名: Chromogen I；N-[(2S,5S)-5-[(1R)-1,2-dihydroxyethyl]-2-hydroxy-2,5-dihydrofuran-3-yl]acetamide
• CAS: 58546-02-4
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: GLYJTEJBNQBAPX-CSMHCCOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.92
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  99.02
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-乙酰胞壁酸 在 sodium hydroxide 作用下， 生成 2-acetamido-2,3-dideoxy-β-D-erythro-hex-2-enofuranose 、 2-acetamido-2,3-dideoxy-α-D-erythro-hex-2-enofuranose 、 3,6-anhydro-MNF 、 3,6-anhydro-MNF 、 2-acetamido-3,6-anhydro-2-deoxy-β-D-glucose 、 2-acetamido-3,6-anhydro-2-deoxy-α-D-glucose
  参考文献：
  名称：

  Thermal decomposition of β-d-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-d-hexopyranoses under neutral conditions

  摘要：

  beta-D-Galactopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-D-glucose (LNB) and beta-D-galactopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-D-galactose (GNB) decompose rapidly upon heating into D-galactose and mono-dehydrated derivatives of the corresponding 2-acetamido-2-deoxy-D-hexoses, including 2-acetamido-2,3-dideoxy-hex-2-enofuranoses and bicyclic 2-acetamido-3,6-anhydro-2-deoxy-hexofuranoses. The decomposition is conducted under neutral conditions where glycosyl linkages are generally believed to be stable. The half-lives of LNB and GNB were 8.1 min and 20 min, respectively, at 90 degrees C and pH 7.5. The pH dependency of decomposition rates suggests that the instabilities are an extension of the conditions for the peeling reaction, often observed with glycans of O-linked glycoproteins under alkaline conditions. Such decomposition under the neutral conditions is commonly observed with 3-O-linked reducing aldoses. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.06.003

文献信息

• Non-catalytic synthesis of Chromogen I and III from N-acetyl-d-glucosamine in high-temperature water
  作者：Mitsumasa Osada、Kazushi Kikuta、Kohei Yoshida、Kazuhide Totani、Makoto Ogata、Taichi Usui

  DOI：10.1039/c3gc41161c

  日期：——

  Non-catalytic synthesis of 2-acetamido-2,3-dideoxy-D-erythro-hex-2-enofuranose (Chromogen I) and 3-acetamido-5-(1′,2′-dihydroxyethyl)furan (Chromogen III) from N-acetyl-D-glucosamine (GlcNAc) was achieved, with the highest yields of 23.0% and 23.1%, respectively, in high-temperature water at 120–220 °C and 25 MPa with a reaction time of 7–39 s.

  非催化合成2-乙酰氨基-2,3-二脱氧-D-赤型-己二-2-呋喃酮糖（色原I）和3-乙酰氨基-5-（1'，2'-二羟乙基）呋喃（色原III）在120-220°C和25 MPa的高温水中，N-乙酰基-D-葡萄糖胺（GlcNAc）的最高收率分别为23.0％和23.1％，反应时间为7-39 s。
• Novel and facile synthesis of furanodictines A and B based on transformation of 2-acetamido-2-deoxy-d-glucose into 3,6-anhydro hexofuranoses
  作者：Makoto Ogata、Takeshi Hattori、Ryota Takeuchi、Taichi Usui

  DOI：10.1016/j.carres.2009.10.007

  日期：2010.1

  A novel synthesis of furanodictines A[2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-glucofuranose (1)] and B [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-mannofuranose (2)] is described starting from 2-acetamido-2-deoxy-D-glucose (G1cNAc). The synthetic protocol is based on deriving the epimeric bicyclic 3,6-anhydro sugars [2-acetamido-3,6-anhydro-2-deoxy-D-glucofuranose (4) and 2-acetamido-3,6-anhydro-2-deoxy-D-mannofuranose (5)] from GlcNAc. Reaction with borate upon heating led to a facile transformation of GlcNAc into the desired epimeric 3,6-anhydro sugars. The C5 hydroxyl group of the 3,6-anhydro compounds 4 and 5 was regioselectively esterified with the isovaleryl chloride to complete the synthesis of furanodictines A and B, respectively. The targets 1 and 2 were synthesized in only two steps requiring no protection/deprotection. (C) 2009 Elsevier Ltd. All rights reserved.