4-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside | 488092-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: p-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside；p-methoxy phenyl galactoside；[(2R,3R,4S,5R,6S)-3,5-dibenzoyloxy-4-hydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methyl benzoate
• CAS: 488092-52-0
• 化学式: C₃₄H₃₀O₁₀
• 分子量: 598.606
• InChiKey: UVPMQCSOQSCWBF-OQTLJYCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 p-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  A practical synthesis of β-d-GlcA-(1→3)-β-d-Gal-(1→3)-β-d-Gal-(1→4)-d-Xyl, a part of the common linkage region of a glycosaminoglycan

  摘要：

  A practical synthesis of beta-D-GlcA-(1 --> 3)-beta-D-Gal-(1 --> 3)-beta-D-Gal-(1 -->4)-beta-D-Xyl-(1 --> OMe) was achieved by coupling of methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate with a trisaccharide acceptor. The trisaccharide acceptor was obtained by condensation of 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 --> 3)-2,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate with methyl 2,3-di-O-benzoyl-beta-D-xylopyranoside, followed by deallylation. The beta-(1 --> 3)-linked disaccharide was prepared readily with p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside as the key synthon. The alpha-(1--> 3)-linkage was formed in considerable amount with galactose mono- and disaccharide trichloroacetimidate donors with C-2 neighboring group participation. CO 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00169-6
• 作为产物：
  描述：

  对甲氧苯基-3-O-烯丙基-β-D-吡喃半乳糖苷 在 palladium dichloride 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 4.0h， 生成 4-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  A practical synthesis of β-d-GlcA-(1→3)-β-d-Gal-(1→3)-β-d-Gal-(1→4)-d-Xyl, a part of the common linkage region of a glycosaminoglycan

  摘要：

  A practical synthesis of beta-D-GlcA-(1 --> 3)-beta-D-Gal-(1 --> 3)-beta-D-Gal-(1 -->4)-beta-D-Xyl-(1 --> OMe) was achieved by coupling of methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate with a trisaccharide acceptor. The trisaccharide acceptor was obtained by condensation of 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 --> 3)-2,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate with methyl 2,3-di-O-benzoyl-beta-D-xylopyranoside, followed by deallylation. The beta-(1 --> 3)-linked disaccharide was prepared readily with p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside as the key synthon. The alpha-(1--> 3)-linkage was formed in considerable amount with galactose mono- and disaccharide trichloroacetimidate donors with C-2 neighboring group participation. CO 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00169-6

文献信息

• Unusual α-glycosylation with galactosyl donors with a C2 ester capable of neighboring group participation
  作者：Langqiu Chen、Fanzuo Kong

  DOI：10.1016/s0040-4039(03)00673-7

  日期：2003.4

  6-O-benzylidene-1-thio-β-d-galactopyranoside (15) as the donor, glycosylation of 2 gave α-linked products only, indicating that 4,6-O-benzylidenation led to α-stereoselectivity in spite of the C2 ester capable of neighboring group participation. Using 15 as the donor, glycosylation of mannose derivatives with 2- or 3-OH's, glucose with 2- or 3-OH's, galactose with 2-, or 3-, or 4-OH's, glucosamine and glucuronic

  4-甲氧基苯基2,3,6-三-O-苯甲酰基-β-d-吡喃葡萄糖苷（2）与异丙基3 - O-烯丙基-2,4,6-三-O-苯甲酰基-（9）或6的糖基化- ø -烯丙基-2,3,4-三ö苯甲酰基-1-硫代β-d吡喃半乳糖苷（7）作为供体，得到的α-和β连接混合物，而用异丙3- ö -氯乙酰基-2- ø -苯甲酰基-4,6- ö -benzylidene-（13）和异丙基3- ö -烯丙基-2- ø -苯甲酰基-4,6- ø -亚苄基-1-硫代-β-β-d吡喃半乳糖苷（15）作为供体，2的糖基化仅产生α-连接的产物，表明尽管C2酯能够相邻基团参与，但4,6- O-亚苄基化仍导致α-立体选择性。使用15作为供体，甘露糖衍生物与2-或3-OH's进行糖基化，葡萄糖与2-或3-OH's进行葡萄糖基化，半乳糖与2-或3-或4-或4-OH's进行半乳糖苷，葡糖胺和葡萄糖醛酸与4-OH进行糖基化。 ，以及带有
• Regioselective Acylation of Diols and Triols: The Cyanide Effect
  作者：Peng Peng、Michael Linseis、Rainer F. Winter、Richard R. Schmidt

  DOI：10.1021/jacs.6b02454

  日期：2016.5.11

  positioned hydroxy groups. As cyanide is capable of various kinds of hydrogen bonding and as it is a quite strong sterically nondemanding base, regioselective O-acylations should be possible at low temperatures even at sterically congested positions, thus permitting formation and also isolation of the kinetic product. Indeed, 1,2-cis-diols, having an equatorial and an axial hydroxy group, benzoyl cyanide

  碳水化合物化学的中心主题包括碳水化合物的结构修饰和寡糖合成。两者都需要受区域选择性保护的构建块，这些构建块主要通过间接多步程序获得。因此，需要针对特定​​羟基的直接保护方法。双氢键最终将区分不同位置的羟基。由于氰化物能够形成各种氢键，并且它是一种非常强的空间要求不高的碱，因此即使在空间拥挤的位置，也应该可以在低温下进行区域选择性 O-酰化，从而允许形成和分离动力学产物。实际上，具有赤道和轴羟基的 1,2-顺式二醇、苯甲酰氰或乙酰氰作为酰化剂，和 DMAP 作为催化剂在 -78°C 下产率热力学上不利的轴向 O-酰化产物；在这些条件下未观察到酰基迁移。这种现象被 3,4-O-未保护的半乳糖和吡喃岩藻糖苷以及 2,3-O-未保护的吡喃甘露糖苷证实。即使对于作为三醇的 3,4,6-O-未保护的吡喃半乳糖苷，轴向 4-O-酰化也明显快于伯 6-羟基的 O-酰化。氢键对这种不寻常的区域选择性的重要性可以通过
• Syntheses of β-(1→6)-branched β-(1→3)-linked d-galactans that exist in the rhizomes of Atractylodes lancea DC
  作者：Aixiao Li、Fanzuo Kong

  DOI：10.1016/j.carres.2005.05.017

  日期：2005.9

  β-(1→6)-linked disaccharide donor 4 . Condensation of 2 with 5 and subsequent selective deacetylation by methanolysis produced the β-(1→6)-linked disaccharide acceptor 7 . Reaction of 7 with 4 , oxidative cleavage of 1-OMP, and trichloroacetimidate formation produced the tetrasaccharide donor 9 . The penta- ( 15 ), the hexa- ( 17 ), and the heptasaccharide donor 19 were synthesized similarly. Meanwhile

  摘要用2,3,4,6-四-O-苯甲酰基-α-d-吡喃半乳糖基三氯乙酰亚氨酸酯（1 ），4-甲氧基苯基2,3,4-三-O-苯甲酰基-β-d-吡喃半乳糖苷（2），6-O-乙酰基-2,3,4-三-O-苯甲酰基-α-d-吡喃半乳糖基三氯乙酰亚氨酸（5），4-甲氧基苯基6-O-乙酰基-2,4-二-O-苯甲酰基-β-d-吡喃半乳糖苷（22）和4-甲氧基苯基2,4,6-三-O-苯甲酰基-β- d-半乳糖吡喃糖苷（26）为关键合成子。将2与1偶联，然后将1-OMP氧化裂解，随后形成三氯乙酰亚氨酸酯，得到β-（1→6）连接的二糖供体4。2与5的缩合以及随后的甲醇解选择性脱乙酰基产生了β-（1→6）连接的二糖受体7。7与4的反应，1-OMP的氧化裂解和三氯乙亚氨酸盐的生成产生了四糖供体9。相似地合成五（15），六（17）和七糖供体19。同时，用22处理1产生β-（1→3）-连接的二糖23和α-（1→3）-连接
• Stereoselective Synthesis of the Hexasaccharide Repeating Unit of the Cell Wall Polysaccharide from<i>Kineosporia aurantiaca</i>VKM Ac-720^TEmploying the Direct Glycosylation with Anomeric Hydroxy Sugars Involving Glycosyl Phthalate Intermediates
  作者：So Mi Park、Dae-Hwan Suk、Kwan Soo Kim

  DOI：10.1080/07328300903003352

  日期：2009.7.29

  Synthesis of a suitably protected form of the hexasaccharide repeating unit of the cell wall polymer from Kineosporia aurantiaca VKM Ac-720(T) has been achieved by the stereoselective direct glycosylation of a trisaccharide acceptor with a trisaccharide donor having an anomeric hydroxy group involving a glycosyl phthalate intermediate. Both the trisaccharide acceptor and the trisaccharide donor were obtained from a common trisaccharide, of which two beta-mannopyranosyl linkages were constructed stereoselectively by employing the direct glycosylation method with the anomeric hydroxy sugar involving a glycosyl phthalate intermediate and the 2'-carboxybenzyl glycoside method, respectively.
• A practical synthesis of β-d-GlcA-(1→3)-β-d-Gal-(1→3)-β-d-Gal-(1→4)-d-Xyl, a part of the common linkage region of a glycosaminoglycan
  作者：Langqiu Chen、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00169-6

  日期：2002.9

  A practical synthesis of beta-D-GlcA-(1 --> 3)-beta-D-Gal-(1 --> 3)-beta-D-Gal-(1 -->4)-beta-D-Xyl-(1 --> OMe) was achieved by coupling of methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate with a trisaccharide acceptor. The trisaccharide acceptor was obtained by condensation of 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 --> 3)-2,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate with methyl 2,3-di-O-benzoyl-beta-D-xylopyranoside, followed by deallylation. The beta-(1 --> 3)-linked disaccharide was prepared readily with p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside as the key synthon. The alpha-(1--> 3)-linkage was formed in considerable amount with galactose mono- and disaccharide trichloroacetimidate donors with C-2 neighboring group participation. CO 2002 Elsevier Science Ltd. All rights reserved.