methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside | 131291-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
• 英文别名: Bz(-3)[TBDPS(-6)]b-Gal1Me；[(2R,3S,4S,5R,6R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,5-dihydroxy-6-methoxyoxan-4-yl] benzoate
• CAS: 131291-07-1
• 化学式: C₃₀H₃₆O₇Si
• 分子量: 536.697
• InChiKey: JHUNCJYGICTEJX-NWFYCVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-甲基苯基4,6-O-苄叉-2,3-二-O-苯甲酰基-1-硫代-β-D-吡喃葡萄糖苷 、 methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以60 %的产率得到methyl 2-O-(4,6-di-O-benzylidene-2,3-di-O-benzoyl-β-D-glucopyranosyl)-3-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactopyranoside
  参考文献：
  名称：

  Regioselective Glycosylation of Mannoside and Galactoside Acceptors Containing 2,4-OH Achieved by Altering Protecting Groups at the 1,3,6-Positions

  摘要：

  DOI：

  10.1021/acs.joc.4c00618
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 三乙胺 、 N,N-二异丙基乙胺 、 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.0h， 生成 methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Regioselective Glycosylation of Mannoside and Galactoside Acceptors Containing 2,4-OH Achieved by Altering Protecting Groups at the 1,3,6-Positions

  摘要：

  DOI：

  10.1021/acs.joc.4c00618

文献信息

• Regioselective Benzoylation of 6-O-Protected and 4,6-O-Diprotected Hexopyranosides as Promoted by Chiral and Achiral Ditertiary 1,2-Diamines
  作者：Guixian Hu、Andrea Vasella

  DOI：10.1002/hlca.200290018

  日期：2002.12

  Monobenzoylation of triols (6-O-silylated glycopyranosides) or diols (4,6-O-benzylidenated glycopyranosides) with benzoyl chloride and triethylamine at −60° to 23° is promoted by catalytic amounts of ditertiary 1,2-diamines. The regioselectivity depends mostly on the structure of the alcohols; it is modulated by the configuration and constitution of the diamines, as shown by comparing the effect of Oriyama's

  三醇（6- Monobenzoylation ö -silylated glycopyranosides）或二醇（4,6- ö在-60℃至23 -benzylidenated glycopyranosides）与苯甲酰氯和三乙胺°通过催化量的二叔1,2-二胺的促进。区域选择性主要取决于醇的结构。通过比较Oriyama催化剂（（S）-1和（R）-1），N，N，N ′，N′-四甲基乙二胺（TMEDA ）的作用可以看出，它受二胺的构型和组成的调节。），N，N，N'，N'-四乙基乙二胺（TEEDA），Et 3 N和EtNMe 2。催化剂的空间位阻会削弱其对反应性的影响。与在Oriyama催化剂存在下外消旋-环己烷-1,2-二醇的单和二苯甲酰基化的适度对映选择性相一致，这些二胺对区域选择性的影响相当有限。尽管与过程简单相关，但是在某些情况下，这些催化剂比单一方法可产生更高的单种苯甲酸酯收率。在制备3-
• Synthesis of specifically deoxygenated ligands related to (1→6)-β-d-galacto-oligosaccharides, and studies on their binding to monoclonal antigalactan antibodies
  作者：Thomas Ziegler、Viliam Pavliak、Tsu-Hsing Lin、Pavol Kováč、Cornelis P.J. Glaudemans

  DOI：10.1016/0008-6215(90)84033-q

  日期：1990.9

  Synthetic deoxygenated derivatives of methyl beta-glycosides of (1----6)-beta-D-galacto-oligosaccharides were prepared, and their binding to antigalactan monoclonal antibodies X24 and J539 (Fab') was studied. The results suggest the involvement of an additional, critical hydrogen bond in the highest affinity subsite (A), which now appears to require two hydrogen bonds from the 2- and 3-hydroxyls of the galactosyl residue to the protein, and one from the protein to O-4 of that residue. The data obtained with a series of oligosaccharides deoxygenated at position 3(1), 3(2), 3(3), 4(1), 4(2), or 4(3) support the binding patterns and subsite-arrangement inferred previously from studies with large numbers of deoxyfluoro-substituted ligands and this family of antibodies.