Abequose | 129567-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Abequose
• 英文别名: 3,6-dideoxy-beta-L-xylo-hexopyranose；(2S,3S,5S,6S)-6-methyloxane-2,3,5-triol
• CAS: 129567-21-1
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: KYPWIZMAJMNPMJ-BXKVDMCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Abequose 在 3 A molecular sieve 、 silver carbonate 、 zinc(II) chloride 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 dibenzyl-(2,4-di-O-benzoyl-3,6-dideoxy-β-L-xylo-hexopyranosyl)-phosphate
  参考文献：
  名称：

  Chemical synthesis of GDP-l-galactose and analogues

  摘要：

  Succinct syntheses for L-galactose, 3-deoxy-L-xylo-hexose (3-deoxy-L-galactose), 6-deoxy-L-galactopyranose (L-fucose) and 3,6-dideoxy-L-xylo-hexose (3,6-dideoxy-L-galactose) have been developed starting from commercially available L-galactono-1,4-lactone. L-Galactose and variants were then converted to the guanosine diphosphate derivatives, via the formation of the anomeric phosphates and coupling to guanosine monophosphate morpholidate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)10094-5
• 作为产物：
  描述：

  Acetic acid (S)-1-((2S,4S)-4-acetoxy-5-hydroxy-tetrahydro-furan-2-yl)-ethyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以1.0 g的产率得到Abequose
  参考文献：
  名称：

  Chemical synthesis of GDP-l-galactose and analogues

  摘要：

  Succinct syntheses for L-galactose, 3-deoxy-L-xylo-hexose (3-deoxy-L-galactose), 6-deoxy-L-galactopyranose (L-fucose) and 3,6-dideoxy-L-xylo-hexose (3,6-dideoxy-L-galactose) have been developed starting from commercially available L-galactono-1,4-lactone. L-Galactose and variants were then converted to the guanosine diphosphate derivatives, via the formation of the anomeric phosphates and coupling to guanosine monophosphate morpholidate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)10094-5

文献信息

• All-in-One Synthesis of 3,6-Dideoxysugars: An Olefin Metathesis–Isomerization Approach
  作者：Hongwei Chen、Zuming Lin、Yuan Meng、Jian Li、Sha-Hua Huang、Ran Hong

  DOI：10.1021/acs.orglett.3c02449

  日期：2023.9.1

  known congeners, has been reported using commercially available methyl lactates in five steps. The essential tandem process involving the olefin cross-metathesis and isomerization steps was enabled by the dual function of Grubbs-II catalyst, affording the products in good yields and providing concise and practical access to a class of biologically important deoxysugars.

  据报道，使用市售的乳酸甲酯分五个步骤集体合成了 3,6-二脱氧糖，包括七种天然已知的同源物。格拉布斯-II 催化剂的双重功能实现了涉及烯烃交叉复分解和异构化步骤的重要串联过程，提供了良好收率的产品，并提供了简洁实用地获得一类具有重要生物学意义的脱氧糖的途径。