2,3,4-tri-O-benzoyl-6-O-bromoacetyl-α-D-galactopyranosyl bromide | 100776-43-0

• 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: 2,3,4-tri-O-benzoyl-6-O-bromoacetyl-α-D-galactopyranosyl bromide
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-dibenzoyloxy-6-bromo-2-[(2-bromoacetyl)oxymethyl]oxan-3-yl] benzoate
• CAS: 100776-43-0
• 化学式: C₂₉H₂₄Br₂O₉
• 分子量: 676.312
• InChiKey: AQVJPQFZBPWMPF-RGFLIBBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-6-O-bromoacetyl-α-D-galactopyranosyl bromide 在 2,4,6-三甲基吡啶 、 silver trifluoromethanesulfonate 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 4.5h， 生成 Methyl O-(2,3,4-tri-O-benzoyl-6-O-bromoacetyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Binding studies on internal immunodeterminants: synthesis of β-(1 → 6)-linked oligosaccharide methyl glycosides having one to four internal d-galactopyranosyl residues flanked by gentiobiose residues

  摘要：

  The oligosaccharide glycosides beta-D-Glc p-(1 --> 6)-beta-D-Glc p-(1 --> 6)-[beta-D-Gal p-(1 --> 6)]n-beta-D-Glc p-(1 --> 6)-beta-D-Glc p-1 --> OMe (n = 1-4) were prepared by a convergent block synthesis. Haloacetyl, tert-butyldiphenylsilyl, and dimethylthexylsilyl groups were used as temporary protective groups for the preparation of the intermediate glycosyl donors and acceptors. The deoxygenated trisaccharide glyco-sides beta-D-Glc p-(1 --> 6)-beta-D-Gal p-(1 --> 6)-4-deoxy-beta-D-xylo-Hex p-1 --> OMe and beta-D-Glc p-(1 --> 6)-4-deoxy-beta-D-xylo-Hex p-(1 --> 6)-beta-D-Gal p-1 --> OMe were also synthesized. The binding of each glycoside to the monoclonal antigalactan antibody IgA 1539 was studied and the results support the previous finding that J539 can bind to internal antigenic epitopes. The data are consistent with the interpretation that subsite C of that antibody binds glucose with a K(a) of approximately 6 (cf. 10.9 for galactose).

  DOI：

  10.1016/s0008-6215(00)90575-5
• 作为产物：
  描述：

  1,2,3,4-tetra-O-benzoyl-β-D-galactopyranose 在 2,6-二甲基吡啶 、 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.84h， 生成 2,3,4-tri-O-benzoyl-6-O-bromoacetyl-α-D-galactopyranosyl bromide
  参考文献：
  名称：

  甲基O-（3-deoxy-3-fluoro-β-d-galactopyranosyl）-（1→6）-O-β-d-galactopyranosyl-（1→6）-3-deoxy-3-fluoro-β的合成-d-吡喃半乳糖苷和相关的nmr研究

  摘要：

  依次对甲基3-脱氧-3-氟-β-D-吡喃半乳糖苷进行三苯甲基化，苯甲酰化和去三苯甲基化，得到结晶的甲基2,4-二-O-苯甲酰基-3-脱氧-3-氟-β-D-吡喃半乳糖苷（9 ），它被用作目标寡糖合成中的初始亲核试剂（16）。用2,3,4-三-O-苯甲酰基-6-O-溴乙酰基-α-D-吡喃半乳糖基溴化物处理9，得到相应的二糖衍生物13，其在O-6'处具有可选择性除去的保护基。13的脱溴乙酰化得到二糖亲核体14，当用2,4,6-三-O-苯甲酰基-3-脱氧-3-氟-α-D-吡喃半乳糖基溴化物处理时，得到完全保护的三糖15。15的脱苯甲酰化得到标题糖苷16。在共聚可力丁存在下，在碱缺陷条件下，用三氟甲烷磺酸银作为促进剂进行缩合反应，得到所需β（反式）产物的优异产率。通过使用各种一维和二维nmr技术，对1H和13C-nmr光谱进行了分析，并确定了JCF和JHF耦合常数。

  DOI：

  10.1016/0008-6215(85)85130-2

文献信息

• Synthesis of p-nitrophenyl β-glycosides of (1→6)-β-d-galactopyranosyl-oligosaccharides
  作者：Göran Ekborg、Branka Vranešić、Apurba K. Bhattacharjee、Pavol Kováč、Cornelis P.J. Glaudemans

  DOI：10.1016/0008-6215(85)85023-0

  日期：1985.10

  Sequential tritylation, benzoylation, and detritylation of p-nitrophenyl beta-D-galactopyranoside gave p-nitrophenyl 2,3,4-tri-O-benzoyl-beta-D-galactopyranoside (2). Reaction of 2 with 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl bromide gave p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl)-(1----6) -2,3,4-tri-O-benzoyl-beta-D-galactopyranoside (4) in 94% yield. Deprotection with

  对硝基苯基β-D-吡喃半乳糖苷的顺序三苯甲基化，苯甲酰化和去三苯甲基化得到对硝基苯基2,3,4-三-O-苯甲酰基-β-D-吡喃半乳糖苷（2）。2与2,3,4,6-四-O-苯甲酰基-α-D-吡喃半乳糖基溴的反应得到对硝基苯基O-（2,3,4,6-四-O-苯甲酰基-β-D-吡喃半乳糖基）-（1 ---- 6）-2,3,4-三-O-苯甲酰基-β-D-吡喃半乳糖苷（4），产率94％。然后用甲醇钠脱保护，得到结晶的对硝基苯基O-（β-D-吡喃半乳糖基）-（1-6）-β-D-吡喃半乳糖苷（5）。2与2,3,4-三-O-苯甲酰基-6-O-溴乙酰基-α-D-吡喃半乳糖基溴化物（3）的缩合反应很容易得到保护的二糖对硝基苯基O-（2,3,4-三- O-苯甲酰基-6-O-溴乙酰基-β-D-吡喃半乳糖基）-（1 ---- 6）-2,3，4-三-O-苯甲酰基-β-D-吡喃半乳糖苷（6），可从其中选择性除去溴乙酰基。
• Synthetic mucin fragments: synthesis of O-sulfo and O-methyl derivatives of allyl O-(β-d-galactopyranosyl)-(1 → 3)-2-acetamido-2-deoxy-α-d-galactopyranoside as potential compounds for sulfotransferases
  作者：Rakesh K. Jain、Conrad F. Piskorz、Khushi L. Matta

  DOI：10.1016/0008-6215(95)00162-m

  日期：1995.10

  galactopyranoside (5), allyl O-(6-O-sulfo-beta-D-galactopyranosyl sodium salt)-(1-->3)-2-acetamido-2-deoxy-6- O-methyl-alpha-D-galactopyranoside (10), allyl O-(beta-D-galactopyranosyl)-(1-->3)-2-acetamido-2-deoxy-6-O-sulfo-alpha- D- galactopyranoside sodium salt (13), allyl O-(6-O-sulfo-beta-D-galactopyranosyl sodium salt)-(1-->3)-2-acetamido-2-deoxy- alpha-D-galactopyranoside (17) and allyl O-(3-O-sulfo-beta-D-galactopyranosyl

  将烯丙基2-乙酰氨基-4,6-O-（4-甲氧基亚苄基）-2-脱氧-α-D-半乳清鸦片核苷（1）与2,3,4,6-四-O-乙酰基-α缩合在氰化汞的存在下，-D-吡喃半乳糖基溴化物（2）或2,3,4-三-O-苯甲酰基-6-O-溴乙酰基-α-D-吡喃半乳糖基溴化物（14）。在所需位置用甲基，磺基或两者选择性取代，然后除去保护基，得到烯丙基O-（β-D-吡喃半乳糖基）-（1→3）-2-乙酰氨基-2-脱氧-6- O-甲基-α-D-吡喃半乳糖苷（5），烯丙基O-（6-O-磺基-β-D-吡喃半乳糖基钠盐）-（1-> 3）-2-乙酰氨基-2-脱氧-6- O-甲基-α-D-吡喃半乳糖苷（10），烯丙基O-（β-D-吡喃半乳糖基）-（1-> 3）-2-乙酰氨基-2-脱氧-6-O-磺基-α-D-吡喃半乳糖苷钠盐（13），烯丙基O-（6-O-磺基-β-D-吡喃半乳糖苷钠盐）-（1-> 3）-2-乙酰氨基-2-脱氧
• Binding studies on internal immunodeterminants: synthesis of β-(1 → 6)-linked oligosaccharide methyl glycosides having one to four internal d-galactopyranosyl residues flanked by gentiobiose residues
  作者：Thomas Ziegler、Heinz Sutoris、Cornelis P.J. Glaudemans

  DOI：10.1016/s0008-6215(00)90575-5

  日期：1992.5

  The oligosaccharide glycosides beta-D-Glc p-(1 --> 6)-beta-D-Glc p-(1 --> 6)-[beta-D-Gal p-(1 --> 6)]n-beta-D-Glc p-(1 --> 6)-beta-D-Glc p-1 --> OMe (n = 1-4) were prepared by a convergent block synthesis. Haloacetyl, tert-butyldiphenylsilyl, and dimethylthexylsilyl groups were used as temporary protective groups for the preparation of the intermediate glycosyl donors and acceptors. The deoxygenated trisaccharide glyco-sides beta-D-Glc p-(1 --> 6)-beta-D-Gal p-(1 --> 6)-4-deoxy-beta-D-xylo-Hex p-1 --> OMe and beta-D-Glc p-(1 --> 6)-4-deoxy-beta-D-xylo-Hex p-(1 --> 6)-beta-D-Gal p-1 --> OMe were also synthesized. The binding of each glycoside to the monoclonal antigalactan antibody IgA 1539 was studied and the results support the previous finding that J539 can bind to internal antigenic epitopes. The data are consistent with the interpretation that subsite C of that antibody binds glucose with a K(a) of approximately 6 (cf. 10.9 for galactose).
• Synthesis of methyl O-(3-deoxy-3-fluoro-β-d-galactopyranosyl)-(1→6)-O-β-d-galactopyranosyl-(1→6)-3-deoxy-3-fluoro -β-d-galactopyranoside and related n.m.r. studies
  作者：Pavol Kováč、Cornelis P.J. Glaudemans、Wie Guo、Tuck C. Wong

  DOI：10.1016/0008-6215(85)85130-2

  日期：1985.7

  Sequential tritylation, benzoylation, and detritylation of methyl 3-deoxy-3-fluoro-beta-D-galactopyranoside gave crystalline methyl 2,4-di-O-benzoyl-3-deoxy-3-fluoro-beta-D-galactopyranoside (9), which was used as the initial nucleophile in the synthesis of the target oligosaccharide (16). Treatment of 9 with 2,3,4-tri-O-benzoyl-6-O-bromoacetyl-alpha-D-galactopyranosyl bromide gave the corresponding

  依次对甲基3-脱氧-3-氟-β-D-吡喃半乳糖苷进行三苯甲基化，苯甲酰化和去三苯甲基化，得到结晶的甲基2,4-二-O-苯甲酰基-3-脱氧-3-氟-β-D-吡喃半乳糖苷（9 ），它被用作目标寡糖合成中的初始亲核试剂（16）。用2,3,4-三-O-苯甲酰基-6-O-溴乙酰基-α-D-吡喃半乳糖基溴化物处理9，得到相应的二糖衍生物13，其在O-6'处具有可选择性除去的保护基。13的脱溴乙酰化得到二糖亲核体14，当用2,4,6-三-O-苯甲酰基-3-脱氧-3-氟-α-D-吡喃半乳糖基溴化物处理时，得到完全保护的三糖15。15的脱苯甲酰化得到标题糖苷16。在共聚可力丁存在下，在碱缺陷条件下，用三氟甲烷磺酸银作为促进剂进行缩合反应，得到所需β（反式）产物的优异产率。通过使用各种一维和二维nmr技术，对1H和13C-nmr光谱进行了分析，并确定了JCF和JHF耦合常数。