2-(Trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 169303-91-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2-(Trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: 2-(trimethylsilyl)ethyl (2-acetamido-2-deoxy-3-O-levulinoyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl)-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside；levulinoyl(-3)GalNAc(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-EtTMS；[(2S,3R,4R,5R,6R)-3-acetamido-2-[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl] 4-oxopentanoate
• CAS: 169303-91-7
• 化学式: C₇₂H₈₉NO₁₈Si
• 分子量: 1284.58
• InChiKey: JQLMPOOZWBDYGF-XUPIFRKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  92
• 可旋转键数：
  35
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  224
• 氢给体数：
  3
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl[phenyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-ulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-non-2-ulopyranosid]onate 、 2-(Trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 以48%的产率得到2-(Trimethylsilyl)ethyl O--(2->6)-O-(2-acetami...
  参考文献：
  名称：

  Hotta, Kenji; Kawase, Tomoko; Ishida, Hideharu, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 7, p. 961 - 976

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(Trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 溶剂黄146 作用下， 反应 24.0h， 以390 mg的产率得到2-(Trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-3-O-levulinyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  A HIGHLY EFFICIENT TOTAL SYNTHETIC ROUTE TO α-SERIES GANGLIOSIDES: GM1α, GD1α, AND GT1α1-2

  摘要：

  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.

  DOI：

  10.1081/car-100103959

文献信息

• 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; Kawase, Tomoko; Ishida, Hideharu, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 7, p. 961 - 976
  作者：Hotta, Kenji、Kawase, Tomoko、Ishida, Hideharu、Kiso, Makoto、Hasegawa, Akira

  DOI：——

  日期：——