dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-azido-α-D-glucopyranoside | 949007-45-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-azido-α-D-glucopyranoside
• CAS: 949007-45-8
• 化学式: C₃₆H₃₅N₄O₁₀P
• 分子量: 714.668
• InChiKey: FPVIYRSLYQVYNJ-NGQZCYGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  51.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  184.45
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-azido-α-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans

  摘要：

  Unnatural chemically modified nucleotide sugars UDP-4-N-3-GlcNAc and UDP-4-N-3-GalNAc were chemically synthesized for the first time. These unnatural UDP sugar products were then tested for incorporation into hyaluronan, heparosan, or chondroitin using polysaccharide synthases. UDP-4-N-3-GlcNAc served as a chain termination substrate for hyaluronan or heparosan synthases; the resulting 4-N-3-GlcNAc-terminated hyaluronan and heparosan were then successfully conjugated with Alexa Fluor 488 DIBO alkyne, demonstrating that this approach is generally applicable for labeling and detection of suitable glycosaminoglycans.

  DOI：

  10.1021/acs.joc.7b01787
• 作为产物：
  描述：

  benzyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-galactopyranoside 在 吡啶 、 iron(III) chloride 、 sodium azide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-azido-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans

  摘要：

  Unnatural chemically modified nucleotide sugars UDP-4-N-3-GlcNAc and UDP-4-N-3-GalNAc were chemically synthesized for the first time. These unnatural UDP sugar products were then tested for incorporation into hyaluronan, heparosan, or chondroitin using polysaccharide synthases. UDP-4-N-3-GlcNAc served as a chain termination substrate for hyaluronan or heparosan synthases; the resulting 4-N-3-GlcNAc-terminated hyaluronan and heparosan were then successfully conjugated with Alexa Fluor 488 DIBO alkyne, demonstrating that this approach is generally applicable for labeling and detection of suitable glycosaminoglycans.

  DOI：

  10.1021/acs.joc.7b01787

文献信息

• WO2007/93769
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of UDP-GlcNAc derivatives modified at OH-4 as potential chain-terminators of chitin biosynthesis
  作者：Thierry Muller、Ramona Danac、Lucy Ball、Sarah J. Gurr、Antony J. Fairbanks

  DOI：10.1016/j.tetasy.2007.05.032

  日期：2007.6

  A series of UDP-GlcNAc derivatives and precursors that have been modified at the 4-position were synthesised from N-acetyl glucosamine as potential chain terminators of chitin biosynthesis. None of the UDP-derivatives or the precursors tested displayed any significant anti-fungal activity in cell adhesion or germination assays on the dermatophyte Trichophyton rubrurn. (c) 2007 Elsevier Ltd. All rights reserved.