1,6-anhydro-2-O-(3,5-dichlorobenzoyl)-3,4-dideoxy-β-D-erythro-hex-3-enopyranose | 138963-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-2-O-(3,5-dichlorobenzoyl)-3,4-dideoxy-β-D-erythro-hex-3-enopyranose
• 英文别名: 1,6-anhydro-2-O-(3,5-dichlorobenzoyl)-3,4-dideoxy-beta-D-erythro-hex-3-enopyranose；[(1S,4R,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yl] 3,5-dichlorobenzoate
• CAS: 138963-03-8
• 化学式: C₁₃H₁₀Cl₂O₄
• 分子量: 301.126
• InChiKey: GTXKTWJCICDPQU-DMDPSCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 、 3,5-二氯苯甲酸 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以77.7%的产率得到1,6-anhydro-2-O-(3,5-dichlorobenzoyl)-3,4-dideoxy-β-D-erythro-hex-3-enopyranose
  参考文献：
  名称：

  Synthesis of D-Allosan from Levoglucosenone

  摘要：

  The stereoselective reduction and cis-dihydroxylation of levoglucosenone (1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyranos-2-ulose), gave D-allosan (1,6-anhydro-beta-D-allopyranose) in high yield.

  DOI：

  10.3987/com-91-5872

文献信息

• Method of manufacturing D-allosan
  申请人：Japan Tobacco Inc.

  公开号：US05457192A1

  公开（公告）日：1995-10-10

  The carbonyl group at the 2-position of levoglucosenone is reduced to obtain a hydroxyl group having a .beta.-configuration. The hydroxyl group having a .beta.-configuration is reversed to an .alpha.-configuration, and hydroxyl groups are added at the 3- and 4-positions in a cis-.alpha. form. Finally, the protective group of the hydroxyl group at the 2-position is eliminated. The reduction of the carbonyl group at the 2-position can be performed such that the levoglucosenone is reacted with aluminum lithium hydride or sodium boron hydride in an appropriate solvent. Reversion of the hydroxyl group having a .beta.-configuration can be performed by the Mitsunobu method or a method having a mesylation step and a step using cesium acetate. The addition of the hydroxyl groups to the 3-and 4-positions in the cis form can be performed by oxidizing the double bond across the 3- and 4-positions with an appropriate oxidizing agent. The elimination of the protective group of the hydroxyl group at the 2-position can be performed under basic conditions in accordance with normal methods. According to the method of the present invention, D-allosan can be obtained stereoselectively in high yield via a smaller number of steps than that of the conventional synthesis method.

  将levoglucosenone的2位上的羰基还原，得到一个具有β构型的羟基。将具有β构型的羟基反转为α构型，并以顺式α的形式在3位和4位上加入羟基。最后，消除2位羟基的保护基。2位羰基还原可以通过将levoglucosenone与适当溶剂中的铝锂或硼氢化钠反应来完成。具有β构型的羟基的反转可以通过Mitsunobu方法或具有甲磺酰化步骤和使用乙酸铯的步骤来完成。以顺式形式在3位和4位上加入羟基可以通过使用适当的氧化剂氧化3位和4位之间的双键来完成。消除2位羟基的保护基可以按照正常方法在碱性条件下完成。根据本发明的方法，可以通过比传统合成方法更少的步骤高选择性地高产地获得D-阿洛糖。
• PROCESS FOR PRODUCING D-ALLOSAN
  申请人：Japan Tobacco Inc.

  公开号：EP0530367A1

  公开（公告）日：1993-03-10

  A process for producing D-allosan (IV) from levoglucosenone (I) in a high yield, which comprises reducing the 2-carbonyl group of levoglucosenone, inverting the configuration of the resultant hydroxyl group from α to β, protecting it by acylation to give a compound (III), conducting α-cis addition of two hydroxyl groups to the double bond of the compound (III), and removing the protective group.

  一种以左旋葡烯酮 (I) 为原料高产制备 D-allosan (IV) 的工艺，该工艺包括还原左旋葡烯酮的 2-羰基，将所得羟基的构型从 α 反转为 β，通过酰化作用对其进行保护，得到化合物 (III)，将两个羟基与化合物 (III) 的双键进行 α-顺式加成，然后除去保护基。
• US5457192A
  申请人：——

  公开号：US5457192A

  公开（公告）日：1995-10-10
• Synthesis of D-Allosan from Levoglucosenone
  作者：Katsuya Matsumoto、Takashi Ebata、Koshi Koseki、Hiroshi Kawakami、Hajime Matsushita

  DOI：10.3987/com-91-5872

  日期：——

  The stereoselective reduction and cis-dihydroxylation of levoglucosenone (1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyranos-2-ulose), gave D-allosan (1,6-anhydro-beta-D-allopyranose) in high yield.