1,2-O-ethylidene-α-D-galactopyranose | 285138-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1,2-O-ethylidene-α-D-galactopyranose
• 英文别名: (3aR,5R,6R,7S,7aR)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6,7-diol
• CAS: 285138-32-1
• 化学式: C₈H₁₄O₆
• 分子量: 206.196
• InChiKey: GXGDQLJREOZCHI-UVPISYNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-ethylidene-α-D-galactopyranose 在 sodium hydride 、 臭氧 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 生成 1,2-O-ethylidene-3,4,6-tri-O-(2-oxo-2-methoxy-ethyl)-α-D-galactopyranose
  参考文献：
  名称：

  Glycosiderophores: Synthesis of tris-hydroxamate siderophores based on a galactose or glycero central scaffold, Fe(III) complexation studies

  摘要：

  A series of five new hexadentate tris-hydroxamate ligands based on a D-galactose or a glycerol scaffold have been synthesized. Protonation and ferric complex formation constants have been determined from solution studies by potentiometric and spectrophotometric titrations. All ligands form 1:1 Fe:L complexes. The calculated pFe values at pH 7.4 span over the range 19.2-23.0 depending on the scaffold and on the length of the spacers between hydroxamate and central scaffold and on the N-methyl substitution. This new kind of artificial siderophores based on a glycoscaffold is of interest as it opens up an easy way to modulate the pFe. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.02.030
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 甲醇 、 sodium tetrahydroborate 、 sodium 、 四丁基碘化铵 作用下， 以 乙腈 为溶剂， 生成 1,2-O-ethylidene-α-D-galactopyranose
  参考文献：
  名称：

  Glycosiderophores: Synthesis of tris-hydroxamate siderophores based on a galactose or glycero central scaffold, Fe(III) complexation studies

  摘要：

  A series of five new hexadentate tris-hydroxamate ligands based on a D-galactose or a glycerol scaffold have been synthesized. Protonation and ferric complex formation constants have been determined from solution studies by potentiometric and spectrophotometric titrations. All ligands form 1:1 Fe:L complexes. The calculated pFe values at pH 7.4 span over the range 19.2-23.0 depending on the scaffold and on the length of the spacers between hydroxamate and central scaffold and on the N-methyl substitution. This new kind of artificial siderophores based on a glycoscaffold is of interest as it opens up an easy way to modulate the pFe. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.02.030

文献信息

• An Efficient Method for the Synthesis of 2,6-Branched Galacto-Oligo­saccharides and Its Applications to the Synthesis of Three Tetrasaccharides and a Hexasaccharide Related to the Arabinogalactans (AGs)
  作者：Jun Ning、Yuetao Yi、Zhe Yao

  DOI：10.1055/s-2003-42109

  日期：——

  An efficient method for the synthesis of 2,6-branched galacto-oligosaccharides has been developed by using 6-O-Ac-2,3,4-tri-O-Bz-α-d-galactopyranosyl trichloroacetimidate, 2,6-di-O-Ac-3,4-di-O-Bz-α-d-galactopyranosyl trichloroacetimidate and 2-O-Ac-3,4,6-tri-O-Bz-α-d-galactopyranosyl trichloroacetimidate as synthons. Three tetrasaccharides and a hexasaccharides related to AGs from plants were readily prepared using this method.

  通过使用6-O-Ac-2,3,4-三-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺、2,6-二-O-Ac-3,4-二-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺和2-O-Ac-3,4,6-三-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺作为合成砌块，开发了一种高效合成2,6-支化半乳寡糖的方法。利用这种方法，可以方便地制备与植物来源的AGs相关的三种四糖和一种六糖。
• Regio- and Stereoselective Synthesis of 1 → 5-Linked α-l-Arabinofuranosyl Oligosaccharides
  作者：Yuguo Du、Qingfeng Pan、Fanzuo Kong

  DOI：10.1055/s-1999-3170

  日期：——

  Regio- and stereoselective synthesis of furanosyl oligosaccharides in moderate to very good yields using arabinofuranosyl trichloroacetimidates as glycosyl donors and unprotected or partially protected glycosides as acceptors was described. A convergent synthesis of 1 → 5-linked α-l-arabinofuranosyl octamer was presented.

  以阿拉伯呋喃糖基三氯乙酰亚氨酸酯为糖基供体，以未保护或部分保护的糖苷为受体，描述了呋喃糖基寡糖的区域和立体选择性合成，产率中等至非常好。介绍了 1 → 5 连接的δ-±-阿拉伯呋喃糖基八聚体的聚合合成。
• Superoxide dismutase-like activity of cobalt(ii) complexes based on a sugar platform
  作者：François Bellot、Renaud Hardré、Giorgio Pelosi、Michel Thérisod、Clotilde Policar

  DOI：10.1039/b508893c

  日期：——

  A SOD-like activity evaluated by a modified McCord–Fridovich test was evidenced for two Co(II) complexes built from “glycoligands” using a sugar platform derived from D-galactose and D-galactal and functionalized by three 2-picolyl groups.

  通过改良的McCord-Fridovich测试评估了类似SOD的活性，证实了由“糖配体”构建的两个Co（II）配合物，其糖平台来自D-半乳糖和D-半乳糖醛，并通过三个2-吡啶基官能团进行官能化。
• SYNTHESIS OF 3-<i>O</i>-ARABINOSYLATED (1→6)-β-<scp>D</scp>-GALACTAN EPITOPES
  作者：Qingfeng Pan、Yuguo Du、Fanzuo Kong*、Jingqi Pan、Mujian Lü

  DOI：10.1081/car-100104865

  日期：2001.4.30

  Two tetrameric arabinogalactans, β-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-(1→6)-[α-L-arabinofuranosyl-(1→3)]-D-galactopyranose (14) and α-L-arabinofuranosyl-(1→3)-β-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-(1→6)-D-galactopyranose (25), which are good candidates for CCRC-M7 epitope characterization, were synthesized efficiently using a convergent strategy. Migration of an acceptor acetyl

  两个四聚阿拉伯半乳聚糖，β- D-吡喃半乳糖-（1→6）-β- D-吡喃半乳糖-（1→6）-[α- L-阿拉伯呋喃糖基- （1→3）]- D-吡喃半乳糖（14）和α -L-阿拉伯呋喃糖基- （1→3）-β- D-吡喃半乳糖基-（1→6）-β- D-吡喃半乳糖基-（1→6）-D-吡喃半乳糖（25），它们是CCRC-M7的良好候选者抗原表位表征，使用收敛策略进行了有效合成。受体乙酰基的迁移被证明是合成的障碍，但是区域选择性糖基化或4- O受体的-苄基保护避免了这个问题，从而可以有效合成1→6连接的目标化合物。
• A convenient synthesis of 1,2-O-benzylidene and 1,2-O-ethylidene derivatives of carbohydrates
  作者：Vitali I. Betaneli、Michael V. Ovchinnikov、Leon V. Backinowsky、Nikolay K. Kochetkov

  DOI：10.1016/s0008-6215(00)80547-9

  日期：1982.9