3,4,6-tri-O-acetyl-1,2-O-<(S)-ethylidene>-α-D-gulopyranose | 37679-97-3

• 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: 3,4,6-tri-O-acetyl-1,2-O-<(S)-ethylidene>-α-D-gulopyranose
• 英文别名: 3,4,6-tri-O-acetyl-1,2-O-<(R)-ethylidene>-α-D-galactopyranose；3,4,6-tri-O-acetyl-1,2-O-<(S)-ethylidene>-α-D-galactopyranose；3,4,6-tri-O-acetyl-1,2-O-<(R)-ethylidene>-α-D-gulopyranose；3,4,6-tri-O-acetyl-1,2-O-[(S)-ethylidene]-α-D-glucopyranose；3,4,6-tri-O-acetyl-1,2-O-ethylidene-α-D-galactopyranose；1,2-O-ethylidene-3,4,6-tri-O-acetyl-α-D-galactopyranose
• CAS: 37679-97-3；38081-36-6；38081-37-7；56687-80-0；56687-81-1；83289-92-3；83289-94-5；83289-95-6；83289-98-9；101144-01-8；101144-02-9；112346-26-6
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: NBWFYJVPTWVPKZ-VUYBJCLPSA-N

物化性质

• 沸点：
  400.4±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-1,2-O-<(S)-ethylidene>-α-D-gulopyranose 在 甲醇 、 lithium hydroxide monohydrate 、 sodium 、 sodium hydride 、 臭氧 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 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-(3-carboxypropyl)-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 sodium tetrahydroborate 、 四丁基碘化铵 作用下， 以 乙腈 、 水 为溶剂， 以71%的产率得到3,4,6-tri-O-acetyl-1,2-O-<(S)-ethylidene>-α-D-gulopyranose
  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

• Synthesis of substituted 2,7-dioxabicyclo[4.1.0]heptanes: 1,2-anhydro-3,4,6-tri-O-benzyl- and 1,2-anhydro-3,4,6-tri-O-(p-bromobenzyl)-α-d-galactopyranose
  作者：Fanzuo Kong、Jingying Du、Heng Shang

  DOI：10.1016/0008-6215(87)80217-3

  日期：1987.5

  1,2-blocked d -galactopyranose ethers, the 1,2-hydroxyl groups were protected with an ethylidene group instead of a 1-ethoxyethylidene group. The key intermediates for the synthesis were 2- O -acetyl-3,4,6-tri- O -benzyl- and 2- O -acetyl-3,4,6-tri- O -( p -bromobenzyl)-β- d -galactopyranosyl fluoride that were prepared from the corresponding, substituted α- d -galactopyranosyl chlorides with silver

  摘要由d-半乳糖经9个步骤合成了标题化合物。为了获得稳定的1，2-嵌段的d-吡喃半乳糖醚，用亚乙基而不是1-乙氧基亚乙基保护1，2-羟基。合成的关键中间体是2-O-乙酰基-3,4,6-三-O-苄基和2-O-乙酰基-3,4,6-三-O-（对溴苄基）-β- d-吡喃半乳糖基氟是由相应的，被氟化银取代的α-d-吡喃半乳糖基氯制备的。用叔丁醇钾在环戊烷中回流下定量测定β-d-吡喃半乳糖基氟的闭环，得到结晶的目标化合物。合成中涉及的大多数反应容易以高产率进行。