methyl 2,4,6-tri-O-benzoyl-3-O-benzyk-1-thio-β-D-galactopyranoside | 146196-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4,6-tri-O-benzoyl-3-O-benzyk-1-thio-β-D-galactopyranoside
• 英文别名: methyl 2,4,6-tri-O-benzoyl-3-O-benzyl-1-thio-β-D-galactopyranoside；[(2R,3S,4S,5R,6S)-3,5-dibenzoyloxy-6-methylsulfanyl-4-phenylmethoxyoxan-2-yl]methyl benzoate
• CAS: 146196-38-5
• 化学式: C₃₅H₃₂O₈S
• 分子量: 612.7
• InChiKey: CMKSDRHCDPWZFN-UEBWFRDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,4,6-tri-O-benzoyl-3-O-benzyk-1-thio-β-D-galactopyranoside 、 2-(Trimethylsilyl)ethyl O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-<(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)>-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-be... 在 4 A molecular sieve 、 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以61%的产率得到2-(Trimethylsilyl)ethyl O-(2,4,6,-tri-O-benzoyl-3-O-benzyl-β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-O-<(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)...
  参考文献：
  名称：

  Terada, Tomohiro; Toyoda, Tsuyoshi; Ishida, Hideharu, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 6, p. 769 - 790

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 3-O-benzyl-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 生成 methyl 2,4,6-tri-O-benzoyl-3-O-benzyk-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  神经节系列神经节苷脂的简便，系统合成：神经节苷脂GM1和GD1a的全合成。

  摘要：

  DOI：

  10.1016/0008-6215(92)80104-9

文献信息

• Study on systematizing the synthesis of the a-series ganglioside glycans GT1a, GD1a, and GM1 using the newly developed N-Troc-protected GM3 and GalN intermediates
  作者：Tatsuya Komori、Akihiro Imamura、Hiromune Ando、Hideharu Ishida、Makoto Kiso

  DOI：10.1016/j.carres.2009.06.009

  日期：2009.8

  A first systematic synthesis of the glycan parts of the a-series gangliosides (GT1a, GD1a, and GM1) utilizing the newly developed N-Troc-protected GM3 and galactosaminyl building blocks is described. The key processes, including the assembly of the GM2 sequence and its conversion into the 3-hydroxy acceptor, were facilitated mainly by the high degree of participation and chemoselective cleavability

  描述了利用新开发的N-Troc保护的GM3和半乳糖胺基结构单元对a系列神经节苷脂（GT1a，GD1a和GM1）的聚糖部分进行的首次系统合成。关键过程，包括GM2序列的组装及其向3-羟基受体的转化，主要是由于半乳糖胺基单元中Troc基团的高度参与性和化学选择性可切割性而促进的。此外，新型GM2受体在与半乳糖基，唾液酸半乳糖基和二唾液酸半乳糖基供体进行糖基化过程中，充当了良好的偶联伴侣，成功地生产了GM1，GD1a和GT1a聚糖。
• Total synthesis of ganglioside GQ1b and the related polysialogangliosides
  作者：Hide-Ki Ishida、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1016/s0957-4166(00)80396-1

  日期：1994.12

  The first total synthesis of ganglio-series gangliosides GQ1b, GT1b and GD1b, which contain α-sialyl-(2→8)-α-sialic acid residue in the structure, will be described. Glycosylation of 2-(trimethylsilyl)ethyl O-(2-acetamido-6-O-benzyl-2-deoxy-3,4-O-iso-propylidene-β-D-galactopyranosyl)-(1→4)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (7) with methyl [phenyl

  将描述在结构中含有α-唾液酸-（2→8）-α-唾液酸残基的神经节系列神经节苷脂GQ1b，GT1b和GD1b的第一全合成。的糖基化2-（三甲基硅烷基）乙基ø - （2-乙酰氨基-6- ø -苄基-2-脱氧-3,4- ø -异亚丙基β-d吡喃半乳糖基） - （1→4） - ø - （2,6-二-O-苄基-β-D-吡喃半乳糖基）-（1→4）-2,3,6-三-O-苄基-β-D-吡喃葡萄糖苷（7）与甲基[苯基5-乙酰氨基-8- ø - （5-乙酰氨基-4,7,8,9-四- ø -乙酰基-3,5-二脱氧D-甘油基-α-D-半乳-2- nonulopyranosylono-1'，9-内酯）-4,7-二-O在乙腈中使用N-碘丁二酰亚胺（NIS）-三氟甲磺酸（TfOH）生成-乙酰基3,5-二甲氧基-2-硫代-D-甘油基-D-半乳糖基-2-壬基吡喃糖苷（8），得到受保护的GD2五糖9，其通过脱-O-异丙基亚丙
• A HIGHLY EFFICIENT TOTAL SYNTHETIC ROUTE TO α-SERIES GANGLIOSIDES: GM1α, GD1α, AND GT1α1-2
  作者：Hiromi Ito、Hideharu Ishida、Makoto Kiso

  DOI：10.1081/car-100103959

  日期：2001.3.31

  A highly efficient total synthetic route to alpha -series gangliosides GM1 alpha, GD1 alpha and GT1 alpha is described. The suitably protected gangliotriose (GgOse3) derivatives, i.e., 2-(trimethylsilyl)ethyl (2-acetamido-2-deoxy-3-O-p-methoxybenzyl-beta -D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzyl-beta -D-galactopyranosyl)-(1 -->4)-2,3,6-tri-O-benzyl-beta -D-glucopyranoside (8) and the corresponding III3-levulinoyl derivative (9), were regioselectively glycosylated with the phenyl 2-thioglycoside of N-acetylneuraminic acid (Neu5Ac) promoted by N-iodosuccinimide (NIS)-trimethylsilyl trifluoromethanesulfonate (TMSOTf) or trifluoromethanesulfonic acid (TfOH) in acetonitrile, to give the desired alpha -Neu5Ac-(2-->6)-gangliotriose (III(6)Neu5AcGgOse3) derivatives as the major products (11 and 12). The p-methoxybenzyl (MPM) group in 11 or the levulinoyl group in 12 was selectively removed, and the resulting 2-(trimethylsilyl)ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha -D-galacto-2-nonulopyranosylonate)-(2-->6)-(2-acetamido-2-deoxy-beta -D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzyl-beta -D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta -D-glucopyranoside (13), a key glycosyl acceptor, was systematically glycosylated with the galactose donor (14), alpha -Neu5Ac-(2-->3)-galactuse donor (15) and alpha -Neu5Ac-(2-->8)-alpha -Neu5Ac-(2-->3)-galactose donor (20) to give the protected GM1 alpha (16, 70%), GD1 alpha (17, 80%) and GT1 alpha (21, 87%) oligosaccharides, respectively, which can be converted to the target gangliosides by the introduction of ceramide and then complete deprotection.
• Hotta, Kenji; Komba, Shiro; Ishida, Hideharu, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 665 - 678
  作者：Hotta, Kenji、Komba, Shiro、Ishida, Hideharu、Kiso, Makoto、Hasegawa, Akira

  DOI：——

  日期：——
• A facile, systematic synthesis of ganglio-series gangliosides: Total synthesis of gangliosides GM1 and GD1a
  作者：Akira Hasegawa、Takao Nagahama、Makoto Kiso

  DOI：10.1016/0008-6215(92)80104-9

  日期：1992.11