3,4-didecyloxy-cyclobut-3-ene-1,2-dione | 61699-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-didecyloxy-cyclobut-3-ene-1,2-dione
• 英文别名: didecyl squarate；3,4-Didecyloxy-cyclobut-3-ene-1,2-dione；3,4-didecoxycyclobut-3-ene-1,2-dione
• CAS: 61699-61-4
• 化学式: C₂₄H₄₂O₄
• 分子量: 394.595
• InChiKey: ISWFUVBWJNNQSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  28
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-didecyloxy-cyclobut-3-ene-1,2-dione 、 (2R,4S,5R,6R)-2-(5-aminopentoxy)-4-hydroxy-5-(2-methylpropanoylamino)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以31 mg的产率得到5-(2-decyloxy-3,4-dioxocyclobut-1-enyl)aminopentyl-[5-N-isobutanoyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl]onic acid
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of N-Acyl Modified Sialic Acids as Inhibitors of Adenoviruses Causing Epidemic Keratoconjunctivitis

  摘要：

  The adenovirus serotype Ad37 binds to and infects human corneal epithelial (HCE) cells through attachment to cellular glycoproteins carrying terminal sialic acids. By use of the crystallographic structure of the sialic acid-interacting domain of the Ad37 fiber protein in complex with sialyllactose, a set of N-acyl modified sialic acids were designed to improve binding affinity through increased hydrophobic interactions. These N-acyl modified sialic acids and their corresponding multivalent human serum albumin (HSA) conjugates were synthesized and tested in Ad37 cell binding and cell infectivity assays. Compounds bearing small substituents were as effective inhibitors as sialic acid. X-ray crystallography and overlays with the Ad37-sialyllactose complex showed that the N-acyl modified sialic acids were positioned in the same orientation as sialic acid. Their multivalent counterparts achieved a strong multivalency effect and were more effective to prevent infection than the monomers. Unfortunately, they were less active as inhibitors than multivalent sialic acid.

  DOI：

  10.1021/jm801609s
• 作为产物：
  描述：

  癸醇 、 方酸 以 苯 为溶剂， 生成 3,4-didecyloxy-cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  BE840884

  摘要：

  公开号：

文献信息

• Carbamate Linker Strategy in Solid-Phase Synthesis of Amino-Functionalized Glycoconjugates for Attachment to Solid Surfaces and Investigation of Protein-Carbohydrate Interactions
  作者：Sara Spjut、Maciej Pudelko、Mirja Hartmann、Mikael Elofsson

  DOI：10.1002/ejoc.200800670

  日期：2009.1

  Amino-functionalized serine-based galactose and glucose neoglycolipids were prepared by solid-phase synthesis using a carbamate strategy for anchoring amino functionalities to a (2-fluoro-4-hydroxy ...

  氨基官能化的丝氨酸基半乳糖和葡萄糖新糖脂是通过固相合成制备的，使用氨基甲酸酯策略将氨基官能团锚定到（2-氟-4-羟基...
• NOVEL METHOD FOR RECOVERY OF SQUARIC ACID MONO ESTERS IN BIOCONJUGATION CHEMISTRY
  申请人：Lundonia Biotech AB

  公开号：EP1438328A1

  公开（公告）日：2004-07-21
• CONJUGATING AMINES
  申请人：Ryan Edward T.

  公开号：US20150031863A1

  公开（公告）日：2015-01-29

  The disclosure provides directly conjugated polysaccharide vaccine molecules and methods related thereto.
• US9616139B2
  申请人：——

  公开号：US9616139B2

  公开（公告）日：2017-04-11
• [EN] NOVEL METHOD FOR RECOVERY OF SQUARIC ACID MONO ESTERS IN BIOCONJUGATION CHEMISTRY<br/>[FR] NOUVEAU PROCEDE DE RECUPERATION DE MONO ESTERS D'ACIDE SQUARIQUE EN CHIMIE DE CONJUGAISON BIOLOGIQUE
  申请人：LUNDONIA BIOTECH AB

  公开号：WO2003035672A1

  公开（公告）日：2003-05-01

  The present invention relates to a biomolecule squaric acid monoamide conjugate of formula (I), as presented in the claims, and to a method for non-polar extraction of a biomolecule squaric acid monoamide conjugate of formula (I), as presented in the claims, obtained after a bioconjugation reaction, wherein said extraction comprises recovering said intermediate by non-polar means.