[(3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-7-hydroxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl 2,2-dimethylpropanoate | 302599-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-7-hydroxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl 2,2-dimethylpropanoate
• CAS: 302599-15-1
• 化学式: C₆₈H₇₅NO₁₆S
• 分子量: 1194.41
• InChiKey: XIBUOZJJDPHXFV-RDXXBRDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  86
• 可旋转键数：
  24
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  211
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  Methyl (2,3,4-tri-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside 、 [(3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-7-hydroxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl 2,2-dimethylpropanoate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以50%的产率得到
  参考文献：
  名称：

  First total synthesis of sialylated and sulfated Lewisx mucin Core 2 structures as potential tumor associated antigens

  摘要：

  Two branched Core 2 structures, (3-O-SO3Na)Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1-->6(NeuAc alpha 2-->3Gal beta 1-->3)GalNAc alpha OMe (1) and its positional isomer NeuAc alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1--> 6(3-OSO3Na-Gal beta 1-->3)GalNAc alpha OMe (2), were chemically synthesized for the first time as potential tumor associated antigens. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00975-8
• 作为产物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 [(3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-7-hydroxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  First total synthesis of sialylated and sulfated Lewisx mucin Core 2 structures as potential tumor associated antigens

  摘要：

  Two branched Core 2 structures, (3-O-SO3Na)Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1-->6(NeuAc alpha 2-->3Gal beta 1-->3)GalNAc alpha OMe (1) and its positional isomer NeuAc alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1--> 6(3-OSO3Na-Gal beta 1-->3)GalNAc alpha OMe (2), were chemically synthesized for the first time as potential tumor associated antigens. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00975-8

文献信息

• First total synthesis of sialylated and sulfated Lewisx mucin Core 2 structures as potential tumor associated antigens
  作者：Bao-Guo Huang、Rakesh K. Jain、Robert D. Locke、James L. Alderfer、Walter A. Tabaczynski、Khushi L. Matta

  DOI：10.1016/s0040-4039(00)00975-8

  日期：2000.8

  Two branched Core 2 structures, (3-O-SO3Na)Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1-->6(NeuAc alpha 2-->3Gal beta 1-->3)GalNAc alpha OMe (1) and its positional isomer NeuAc alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1--> 6(3-OSO3Na-Gal beta 1-->3)GalNAc alpha OMe (2), were chemically synthesized for the first time as potential tumor associated antigens. (C) 2000 Elsevier Science Ltd. All rights reserved.