3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 127542-53-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• 英文别名: 3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 2,3,6-tri-O-benzoyl-4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside；[(2R,3R,4S,5R,6R)-3-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4-dibenzoyloxy-5-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dibenzoyloxy-6-[3-hexadecylsulfonyl-2-(hexadecylsulfonylmethyl)propoxy]oxan-2-yl]methyl benzoate
• CAS: 127542-53-4
• 化学式: C₉₉H₁₃₄O₃₀S₂
• 分子量: 1868.27
• InChiKey: NPJNXYUILMDJDR-MOQIEYSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.6
• 重原子数：
  131
• 可旋转键数：
  69
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  403
• 氢给体数：
  0
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以95%的产率得到3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 4-O-(α-D-galactopyranosyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Prespacer glycosides in glycoconjugate chemistry. Dibromoisobutyl (DIB) glycosides for the synthesis of neoglycolipids, neoglycoproteins, neoglycoparticles, and soluble glycosides

  摘要：

  DOI：

  10.1021/jo00299a044
• 作为产物：
  描述：

  3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 间氯过氧苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 以89%的产率得到3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Prespacer glycosides in glycoconjugate chemistry. Dibromoisobutyl (DIB) glycosides for the synthesis of neoglycolipids, neoglycoproteins, neoglycoparticles, and soluble glycosides

  摘要：

  DOI：

  10.1021/jo00299a044

文献信息

• Synthesis of double-chain bis-sulfone neoglycolipids of the 2″-, 3″-, 4″-, and 6″-deoxyglobotrioses
  作者：Zhang Zhiyuan、Göran Magnusson

  DOI：10.1016/0008-6215(94)84006-7

  日期：1994.9

  Me3SiCH2CH2 2''-, 3''-, 4''-, and 6''-deoxyglobotriosides. Transformation of the protected Me3SiCH2CH2 globotriosides into the corresponding trichloroacetimidates proceeded, via the hemiacetals, in 91-96% over-all yield. Glycosylation of 3-(hexadecylsulfonyl-2-[hexadecylsulfonyl)methyl]propanol with the trichloroacetimidates, followed by removal of protecting groups, gave the title neoglycolipids.

  2-（三甲基甲硅烷基）乙基（Me3SiCH2CH2）2,3,6-三-O-苯甲酰基-4-O-（2,3-二-O-苯甲酰基-6-Op-甲氧基苄基-β-D-吡喃半乳糖基-β-用不同的2-，3-，4-或6-“脱氧-D-半乳糖”衍生物将D-吡喃葡萄糖苷糖基化，得到相应的脱氧三糖。除去保护基团得到Me3SiCH2CH2 2''-，3''- ，4''-和6''-脱氧globotriosides。通过半缩醛，将保护的Me3SiCH2CH2 globotriosides转化为相应的三氯乙酰亚胺酯，总收率为91-96％。3-（十六烷基磺酰基-2- [十六烷基磺酰基]的糖基化甲基]丙醇与三氯乙亚氨酸酯，然后除去保护基，得到标题新糖脂。
• MAGNUSSON, GORAN;AHLFORS, STEFAN;DAHMEN, JAN;JANSSON, KARL;NILSSON, ULF;N+, J. ORG. CHEM., 55,(1990) N2, C. 3932-3946
  作者：MAGNUSSON, GORAN、AHLFORS, STEFAN、DAHMEN, JAN、JANSSON, KARL、NILSSON, ULF、N+

  DOI：——

  日期：——