(2R,3R,4S,5R,6R)-2-[(2R)-3-hexadecoxy-2-methoxypropoxy]-3-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane | 180714-38-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2R,3R,4S,5R,6R)-2-[(2R)-3-hexadecoxy-2-methoxypropoxy]-3-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 180714-38-9
• 化学式: C₄₈H₇₂O₈
• 分子量: 777.095
• InChiKey: NRNATRGPVGIXFX-BTINMGIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  56
• 可旋转键数：
  32
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-[(2R)-3-hexadecoxy-2-methoxypropoxy]-3-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以96%的产率得到(2R,3S,4S,5R,6R)-6-[(2R)-3-hexadecoxy-2-methoxypropoxy]-2-(hydroxymethyl)-5-methoxyoxane-3,4-diol
  参考文献：
  名称：

  Synthesis and Growth Inhibitory Properties of Glycosides of 1-O-Hexadecyl-2-O-methyl-sn-glycerol, Analogs of the Antitumor Ether Lipid ET-18-OCH₃ (Edelfosine)

  摘要：

  Glycosylated antitumor ether lipids (GAELs), analogs of 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine (1, ET-18-OCH3, edelfosine), were synthesized in good overall yields by glycosylation of 1-O-alkyl-2-O-methyl-sn-glycerol and tested for in vitro antineoplastic activity against a variety of murine and human tumor cell lines. Stereospecific glycosylation was achieved by the use of 2-O-acetyl-3,4,6-tri-O-benzylglucopyranosyl and -mannopyranosyl trichloroacetimidates as donors, with trimethylsilyl trifluoromethanesulfonate as catalyst in the presence of molecular sieves at -78 degrees C. The GAELs differ from 1 in having the sn-3-phosphocholine residue replaced by one of the following monosaccharide residues: beta- and alpha-2-deoxy-D-arabino-hexopyranosyl, alpha-D-mannopyranosyl, 2-O-methyl-beta-D-glucopyranosyl, and 2-O-methyl-alpha-D-mannopyranosyl. 1-O-Hexadecyl-2-O-methyl-3-O-(2'-deoxy-beta-D-arabino-hexopyranosyl)-sn-glycerol (2) was more effective than 1 in inhibiting the growth of MCF-7 (human breast cancer) and its adriamycin-resistant form MCF-7/adriamycin, and murine Lewis lung cancer. cells. 2-Deoxy-beta-D-arabino-hexopyranoside 2 was also an effective growth inhibitor of two drug-resistant leukemic cell lines, P388/Adr and L1210/vmdr.

  DOI：

  10.1021/jm960164j
• 作为产物：
  描述：

  1-O-hexadecyl-3-O-(p-methoxyphenyl)-sn-glycerol 在 cerium nitrate 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氨 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.42h， 生成 (2R,3R,4S,5R,6R)-2-[(2R)-3-hexadecoxy-2-methoxypropoxy]-3-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
  参考文献：
  名称：

  Synthesis and Growth Inhibitory Properties of Glycosides of 1-O-Hexadecyl-2-O-methyl-sn-glycerol, Analogs of the Antitumor Ether Lipid ET-18-OCH₃ (Edelfosine)

  摘要：

  Glycosylated antitumor ether lipids (GAELs), analogs of 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine (1, ET-18-OCH3, edelfosine), were synthesized in good overall yields by glycosylation of 1-O-alkyl-2-O-methyl-sn-glycerol and tested for in vitro antineoplastic activity against a variety of murine and human tumor cell lines. Stereospecific glycosylation was achieved by the use of 2-O-acetyl-3,4,6-tri-O-benzylglucopyranosyl and -mannopyranosyl trichloroacetimidates as donors, with trimethylsilyl trifluoromethanesulfonate as catalyst in the presence of molecular sieves at -78 degrees C. The GAELs differ from 1 in having the sn-3-phosphocholine residue replaced by one of the following monosaccharide residues: beta- and alpha-2-deoxy-D-arabino-hexopyranosyl, alpha-D-mannopyranosyl, 2-O-methyl-beta-D-glucopyranosyl, and 2-O-methyl-alpha-D-mannopyranosyl. 1-O-Hexadecyl-2-O-methyl-3-O-(2'-deoxy-beta-D-arabino-hexopyranosyl)-sn-glycerol (2) was more effective than 1 in inhibiting the growth of MCF-7 (human breast cancer) and its adriamycin-resistant form MCF-7/adriamycin, and murine Lewis lung cancer. cells. 2-Deoxy-beta-D-arabino-hexopyranoside 2 was also an effective growth inhibitor of two drug-resistant leukemic cell lines, P388/Adr and L1210/vmdr.

  DOI：

  10.1021/jm960164j

文献信息

• US6153736A
  申请人：——

  公开号：US6153736A

  公开（公告）日：2000-11-28
• Synthesis and Growth Inhibitory Properties of Glycosides of 1-<i>O</i>-Hexadecyl-2-<i>O</i>-methyl-<i>sn</i>-glycerol, Analogs of the Antitumor Ether Lipid ET-18-OCH₃ (Edelfosine)
  作者：José R. Marino-Albernas、Robert Bittman、Andrew Peters、Eric Mayhew

  DOI：10.1021/jm960164j

  日期：1996.1.1

  Glycosylated antitumor ether lipids (GAELs), analogs of 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine (1, ET-18-OCH3, edelfosine), were synthesized in good overall yields by glycosylation of 1-O-alkyl-2-O-methyl-sn-glycerol and tested for in vitro antineoplastic activity against a variety of murine and human tumor cell lines. Stereospecific glycosylation was achieved by the use of 2-O-acetyl-3,4,6-tri-O-benzylglucopyranosyl and -mannopyranosyl trichloroacetimidates as donors, with trimethylsilyl trifluoromethanesulfonate as catalyst in the presence of molecular sieves at -78 degrees C. The GAELs differ from 1 in having the sn-3-phosphocholine residue replaced by one of the following monosaccharide residues: beta- and alpha-2-deoxy-D-arabino-hexopyranosyl, alpha-D-mannopyranosyl, 2-O-methyl-beta-D-glucopyranosyl, and 2-O-methyl-alpha-D-mannopyranosyl. 1-O-Hexadecyl-2-O-methyl-3-O-(2'-deoxy-beta-D-arabino-hexopyranosyl)-sn-glycerol (2) was more effective than 1 in inhibiting the growth of MCF-7 (human breast cancer) and its adriamycin-resistant form MCF-7/adriamycin, and murine Lewis lung cancer. cells. 2-Deoxy-beta-D-arabino-hexopyranoside 2 was also an effective growth inhibitor of two drug-resistant leukemic cell lines, P388/Adr and L1210/vmdr.