[(2R)-2-benzoyloxy-2-[(2S,3S,4R)-3,4-dibenzoyloxy-5-bromooxolan-2-yl]ethyl] benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R)-2-benzoyloxy-2-[(2S,3S,4R)-3,4-dibenzoyloxy-5-bromooxolan-2-yl]ethyl] benzoate
• 化学式: C₃₄H₂₇BrO₉
• 分子量: 659.487
• InChiKey: VQNNBEUWJKGBHO-LSZMOXLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R)-2-benzoyloxy-2-[(2S,3S,4R)-3,4-dibenzoyloxy-5-bromooxolan-2-yl]ethyl] benzoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.17h， 生成 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of β-d-Galf-(1−3)-d-GlcNAc by the Trichloroacetamidate Method and of β-d-Galf-(1−6)-d-GlcNAc by SnCl₄-Promoted Glycosylation

  摘要：

  In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. beta-D-Galf-(1-3)-D-GlcNAc (1) was prepared by employing the trichloroacetamidate procedure for the glycosylation step, The mild conditions of this reaction are appropriate for condensation of 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl trichloroacetamidate (6) with acid-labile benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside (3). On the other hand, tin(IV) chloride promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (11) with penta-O-benzoyl-alpha,beta-D-galactofuranose (4) gave the derivative of beta-D-Galf-(1-6)-D-GlcNAc (2) in 78% yield.

  DOI：

  10.1021/ol9905811
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 硫酸 、 氢溴酸 、 三氯化铁 、 溶剂黄146 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 [(2R)-2-benzoyloxy-2-[(2S,3S,4R)-3,4-dibenzoyloxy-5-bromooxolan-2-yl]ethyl] benzoate
  参考文献：
  名称：

  Improved Chemical Synthesis of UDP-Galactofuranose

  摘要：

  [GRAPHICS]A reliable and efficient synthetic route to UDP-alpha -D-galactofuranose (UDP-Galf) has been developed. Reaction of UMP-N-methylimidazolide with Galf 1-phosphate proceeds rapidly to provide UDP-Galf with excellent reproducibility and in a yield approximately twice as high as those reported previously.

  DOI：

  10.1021/ol016170d

文献信息

• The first chemical synthesis of UDP-α-D-galactofuranose
  作者：Yury E. Tsvetkov、Andrei V. Nikolaev

  DOI：10.1039/b000210k

  日期：——

  Uridine 5′-diphosphate α-D-galactofuranose, which is likely to be a biochemical donor of D-galactofuranosyl residues in Nature, is synthesized from α-D-galactofuranosyl phosphate and uridine 5′-monophosphate.

  尿苷5'-二磷酸α-D-半乳糖呋喃糖，可能是自然界中D-半乳糖呋喃糖残基的生物化学供体，由α-D-半乳糖呋喃糖磷酸和尿苷5'-单磷酸合成。
• Improved Chemical Synthesis of UDP-Galactofuranose
  作者：Allison L. Marlow、Laura L. Kiessling

  DOI：10.1021/ol016170d

  日期：2001.8.9

  [GRAPHICS]A reliable and efficient synthetic route to UDP-alpha -D-galactofuranose (UDP-Galf) has been developed. Reaction of UMP-N-methylimidazolide with Galf 1-phosphate proceeds rapidly to provide UDP-Galf with excellent reproducibility and in a yield approximately twice as high as those reported previously.
• Synthesis of β-<scp>d</scp>-Gal<i>f</i>-(1−3)-<scp>d</scp>-GlcNAc by the Trichloroacetamidate Method and of β-<scp>d</scp>-Gal<i>f</i>-(1−6)-<scp>d</scp>-GlcNAc by SnCl₄-Promoted Glycosylation
  作者：Carola Gallo-Rodriguez、Lucia Gandolfi、Rosa M. de Lederkremer

  DOI：10.1021/ol9905811

  日期：1999.7.1

  In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. beta-D-Galf-(1-3)-D-GlcNAc (1) was prepared by employing the trichloroacetamidate procedure for the glycosylation step, The mild conditions of this reaction are appropriate for condensation of 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl trichloroacetamidate (6) with acid-labile benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside (3). On the other hand, tin(IV) chloride promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (11) with penta-O-benzoyl-alpha,beta-D-galactofuranose (4) gave the derivative of beta-D-Galf-(1-6)-D-GlcNAc (2) in 78% yield.