[1(1')Z]-1-deoxy-1-(dibenzyloxyphosphoryl)methylidene-2,3,4,6-tetra-O-tert-butyldimethylsilyl-D-galactopyranose | 1160299-45-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1(1')Z]-1-deoxy-1-(dibenzyloxyphosphoryl)methylidene-2,3,4,6-tetra-O-tert-butyldimethylsilyl-D-galactopyranose
• 英文别名: [(2R,3S,4S,5R,6Z)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-[[oxido-bis(phenylmethoxy)phosphaniumyl]methylidene]oxan-4-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1160299-45-5
• 化学式: C₄₅H₈₁O₈PSi₄
• 分子量: 893.449
• InChiKey: UYMCNAAUDCRIIL-BWUAJDFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.98
• 重原子数：
  58
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  87.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [1(1')Z]-1-deoxy-1-(dibenzyloxyphosphoryl)methylidene-2,3,4,6-tetra-O-tert-butyldimethylsilyl-D-galactopyranose 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 1.5h， 生成
  参考文献：
  名称：

  Synthesis of Three C ‐Glycoside Analogues of UDP‐Galactopyranose as Conformational Probes for the Mutase‐Catalyzed Furanose/Pyranose Interconversion

  摘要：

  AbstractUDP‐galactopyranose mutase (UGM) catalyzes the isomerization of UDP‐galactopyranose (UDP‐Galp) into UDP‐galactofuranose (UDP‐Galf), an essential step of the mycobacterial cell wall biosynthesis. In order to probe the UGM binding pocket, we synthesized the α‐ and β‐C‐glycosidic analogues of UDP‐galacopyranose along with the corresponding UDP‐exo‐galactal. Preliminary inhibition evaluation indicated that UDP‐exo‐galactal inhibits UGM with a binding affinity similar to that of UDP‐α‐C‐galactopyranose.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200801249
• 作为产物：
  描述：

  2,3,4,6-tetra-O-tert-butyldimethylsilyl-1-(dibenzyloxyphosphoryl)methyl-α-D-galactopyranose 在 吡啶 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以626 mg的产率得到[1(1')Z]-1-deoxy-1-(dibenzyloxyphosphoryl)methylidene-2,3,4,6-tetra-O-tert-butyldimethylsilyl-D-galactopyranose
  参考文献：
  名称：

  Synthesis of Three C ‐Glycoside Analogues of UDP‐Galactopyranose as Conformational Probes for the Mutase‐Catalyzed Furanose/Pyranose Interconversion

  摘要：

  AbstractUDP‐galactopyranose mutase (UGM) catalyzes the isomerization of UDP‐galactopyranose (UDP‐Galp) into UDP‐galactofuranose (UDP‐Galf), an essential step of the mycobacterial cell wall biosynthesis. In order to probe the UGM binding pocket, we synthesized the α‐ and β‐C‐glycosidic analogues of UDP‐galacopyranose along with the corresponding UDP‐exo‐galactal. Preliminary inhibition evaluation indicated that UDP‐exo‐galactal inhibits UGM with a binding affinity similar to that of UDP‐α‐C‐galactopyranose.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200801249