methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside | 108999-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside；methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside；methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside；Gal2Ac3Ac4Ac6Ac(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]b-Gal1Me；[(2R,3S,4S,5R,6R)-4,5-dibenzoyloxy-6-methoxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl] benzoate
• CAS: 108999-02-6
• 化学式: C₄₂H₄₄O₁₈
• 分子量: 836.801
• InChiKey: NBOGMAZIQQLGSI-DNXGOYFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  60
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 吡啶 、 2,4-二甲基吡啶 、 silver trifluoromethanesulfonate 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of 1→6 Linked Manno-, Gluco-, and Galactopyranose Di-, Tri-, and Tetrasaccharides Via Orthoester Intermediates

  摘要：

  1-->6 Linked manno-, gluco-, and galactopyranose di-, tri-, and tetrasaccharides with 1,2-trans glycosidic linkages were concisely and effectively synthesized using peracetylated glycosyl bromides as the donors and unprotected or partially protected glycopyranosides as the accepters via orthoester intermediates.

  DOI：

  10.1080/07328300008544122
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 吡啶 、 2,4-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of 1→6 Linked Manno-, Gluco-, and Galactopyranose Di-, Tri-, and Tetrasaccharides Via Orthoester Intermediates

  摘要：

  1-->6 Linked manno-, gluco-, and galactopyranose di-, tri-, and tetrasaccharides with 1,2-trans glycosidic linkages were concisely and effectively synthesized using peracetylated glycosyl bromides as the donors and unprotected or partially protected glycopyranosides as the accepters via orthoester intermediates.

  DOI：

  10.1080/07328300008544122

文献信息

• Stannylene Activation in Glycoside Synthesis: Regioselective Glycosidations at the Primary Position of Galactopyranosides Unprotected in the 2-, 3-, 4-, and 6-Positions
  作者：Per J. Garegg、Jean-Luc Maloisel、Stefan Oscarson

  DOI：10.1055/s-1995-3918

  日期：1995.4

  Stannylene activation with dibutyltin oxide of methyl D-galactopyranosides and of methyl β-D-glucopyranoside, respectively, followed by glycosidation with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide promoted by tetrabutylammonium iodide, or followed by glycosidation with ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside, or ethyl 2,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside, or ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside, the latter four glycosyl donors being promoted by dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST), led to regioselective glycosidation at the 6-OH of the stannylene glycosyl acceptors. This selectivity was not observed in the absence of stannylene activation.

  分别用二丁基氧化锡活化甲基 D-吡喃半乳糖苷和甲基 δ-D-吡喃葡萄糖苷，然后用 2,3,4,6- O-四苄基-δ-D-吡喃葡萄糖基溴化物在四丁基碘化铵的促进下进行糖化，或用乙基 2,3,4,6- O-四苯甲酰基-1-硫代-δ-D-吡喃葡萄糖苷进行糖化、或乙基 2,3,4,6-O-四乙酰基-2-脱氧-2-酞酰亚胺基-1-硫代-δ-D-吡喃葡萄糖苷，或乙基 2,3,4,6-O-四苯甲酰基-1-硫代-δ-D-吡喃甘露糖苷、在三氟甲磺酸二甲基（甲硫基）锍（DMTST）的促进下，后四种糖基供体在链烯糖基受体的 6-OH 处发生了区域选择性糖苷化反应。在没有锡烯活化的情况下，则观察不到这种选择性。
• Efficient chemical synthesis of methyl β-glycosides of β-(1→6)-linked d-galacto-oligosaccharides by a stepwise and a blockwise approach
  作者：Pavol Kováč

  DOI：10.1016/s0008-6215(00)90266-0

  日期：1986.10

  disaccharide 12 was also obtained by the reaction of 1,2,3,4-tetra-O-benzoyl-6-O-bromoacetyl-beta-D-galactopryanose (6) with 1 in the presence of trimethylsilyl trifluoromethane-sulfonate. Similarly, the trisaccharide 18 and the tetrasaccharide 20 were obtained by the treatment of 13, respectively, with 1 and 15, showing that, as with their 1-O-acetyl counterparts, beta-1-benzoates of saccharides bearing at O-2

  甲基2,3,4-三-O-苯甲酰基-β-D-吡喃半乳糖苷（1）的溴乙酰化反应，然后用1,1-二氯甲基甲基醚将生成的6-O-溴乙酰基衍生物2的甲氧基裂解，3，4-三-O-苯甲酰基-6-O-溴乙酰基-α-D-吡喃半乳糖基氯（3）。三氟甲磺酸银促进3与1的反应，得到甲基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（12），在其非还原端基的O-6处带有可选择性除去的溴乙酰基。将其O-脱溴乙酰化，并将形成的二糖亲核试剂15再次用3处理，得到类似的三糖18。重复该反应序列，得到类似的四糖20，显示了逐步构建标题寡糖的可行性。3与1,2,3,4-四-O-苯甲酰基-α-（7）和β-D-吡喃半乳糖（5）的相似反应分别得到O-（2,3,4-tri-O-苯甲酰基-6-O-溴乙酰基-β-D-吡喃半乳糖基）-（1
• Coupling reactions of O-(trimethylsilyl) glycosides and 6-O-(tert-butyldiphenylsilyl)-protected galactosides in the presence of trimethylsilyl triflate. A new method of forming .beta.-(1 .fwdarw. 6)-oligosaccharidic linkages
  作者：Eugenia M. Nashed、Cornelis P. J. Glaudemans

  DOI：10.1021/jo00287a026

  日期：1989.12
• NASHED, EUGENIA M.;GLAUDEMANS, CORNELIS P. J., J. ORG. CHEM., 54,(1989) N6, C. 6116-6118
  作者：NASHED, EUGENIA M.、GLAUDEMANS, CORNELIS P. J.

  DOI：——

  日期：——