methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-3,5-diacetyloxy-2-[(2R,3R,4S,5R,6R)-4-acetyloxy-6-[(E,2S,3R)-2-amino-3-benzoyloxyoctadec-4-enoxy]-5-benzoyloxy-2-(benzoyloxymethyl)oxan-3-yl]oxy-6-(benzoyloxymethyl)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate | 124477-24-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-3,5-diacetyloxy-2-[(2R,3R,4S,5R,6R)-4-acetyloxy-6-[(E,2S,3R)-2-amino-3-benzoyloxyoctadec-4-enoxy]-5-benzoyloxy-2-(benzoyloxymethyl)oxan-3-yl]oxy-6-(benzoyloxymethyl)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 124477-24-3
• 化学式: C₈₄H₁₀₆N₂O₃₁
• 分子量: 1639.76
• InChiKey: AXNUVKWZIWMCHD-KBCNRSDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  117.0
• 可旋转键数：
  43.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  426.1
• 氢给体数：
  2.0
• 氢受体数：
  32.0

反应信息

• 作为反应物：
  描述：

  棕榈酸 、 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-3,5-diacetyloxy-2-[(2R,3R,4S,5R,6R)-4-acetyloxy-6-[(E,2S,3R)-2-amino-3-benzoyloxyoctadec-4-enoxy]-5-benzoyloxy-2-(benzoyloxymethyl)oxan-3-yl]oxy-6-(benzoyloxymethyl)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-β-D-galactopyranosyl)-(1->4)-O-(3-O-acetyl-2,6-di-O-benzoyl-β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-3-O-benz...
  参考文献：
  名称：

  Synthetic Studies on Sialoglycoconjugates 89: Synthesis of Ganglioside GM₃and KDN-GM₃Containing Different Carbon-Chain Length Fatty Acyl Groups at the Ceramide Residue

  摘要：

  Ganglioside GM(3) and KDN-ganglioside GM(3), containing hexanoyl, decanoyl, and hexadecanoyl groups at the ceramide moiety have been synthesized. Selective reduction of the azido group in O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D -gIycero-alpha-D-galacro-2-nonulopyranosylonate)-(2-->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-beta-D-galactopyranosyl) (1-->4)-O-(3-O-acetyl-2,6-di-O-benzoyl-beta-D-glucopyranosyl)-(1-->1)-(2S,3R,4E)-2-azid-3-O-benzoyl-4-octadecene-1,3-diol (1) and O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-gIycero-alpha-D-galacto-2- nonulopyranosylonate)-(2-->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-beta-D-galactopyranosyl)-(1-->4)-O-(3-O-acetyl-2,6-di-O-benzoyl-beta-D-glucopyranosyl)-(1-->1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene- 1,3-diol (2), coupling with hexanoic, decanoic, and hexadecanoic acids, O-deacylation, and de-esterification gave the title gangliosides GM(3) (11 similar to 13) and KDN-GM(3) (14 similar to 16) in good yields. On the other hand, O-deacylation of 1 and subsequent de-esterification gave 2-azido-sphingosine containing-GM(3) analogue 17, which was converted into lyso-GM(3), in which no fatty acyl group was substituted at the sphingosine residue, by selective reduction of the azido group.

  DOI：

  10.1080/07328309608005680
• 作为产物：
  描述：

  O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-β-D-galactopyranosyl)-(1->4)-O-(3-O-acetyl-2,6-di-O-benzoyl-β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-azido-... 在 吡啶 、 硫化氢 作用下， 反应 48.0h， 生成 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-3,5-diacetyloxy-2-[(2R,3R,4S,5R,6R)-4-acetyloxy-6-[(E,2S,3R)-2-amino-3-benzoyloxyoctadec-4-enoxy]-5-benzoyloxy-2-(benzoyloxymethyl)oxan-3-yl]oxy-6-(benzoyloxymethyl)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Synthetic Studies on Sialoglycoconjugates 89: Synthesis of Ganglioside GM₃and KDN-GM₃Containing Different Carbon-Chain Length Fatty Acyl Groups at the Ceramide Residue

  摘要：

  Ganglioside GM(3) and KDN-ganglioside GM(3), containing hexanoyl, decanoyl, and hexadecanoyl groups at the ceramide moiety have been synthesized. Selective reduction of the azido group in O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D -gIycero-alpha-D-galacro-2-nonulopyranosylonate)-(2-->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-beta-D-galactopyranosyl) (1-->4)-O-(3-O-acetyl-2,6-di-O-benzoyl-beta-D-glucopyranosyl)-(1-->1)-(2S,3R,4E)-2-azid-3-O-benzoyl-4-octadecene-1,3-diol (1) and O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-gIycero-alpha-D-galacto-2- nonulopyranosylonate)-(2-->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-beta-D-galactopyranosyl)-(1-->4)-O-(3-O-acetyl-2,6-di-O-benzoyl-beta-D-glucopyranosyl)-(1-->1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene- 1,3-diol (2), coupling with hexanoic, decanoic, and hexadecanoic acids, O-deacylation, and de-esterification gave the title gangliosides GM(3) (11 similar to 13) and KDN-GM(3) (14 similar to 16) in good yields. On the other hand, O-deacylation of 1 and subsequent de-esterification gave 2-azido-sphingosine containing-GM(3) analogue 17, which was converted into lyso-GM(3), in which no fatty acyl group was substituted at the sphingosine residue, by selective reduction of the azido group.

  DOI：

  10.1080/07328309608005680

文献信息

• HASEGAWA, AKIRA;MURASE, TAKATOSHI;MORITA, MINORU;ISHIDA, HIDEHARU;KISO, M+, J. CARBOHYDR. CHEM., 9,(1990) N-3, C. 201-214
  作者：HASEGAWA, AKIRA、MURASE, TAKATOSHI、MORITA, MINORU、ISHIDA, HIDEHARU、KISO, M+

  DOI：——

  日期：——