(2R,3S,4R,6R)-6-[(2R)-3-hexadecoxy-2-methoxypropoxy]-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane | 180714-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,6R)-6-[(2R)-3-hexadecoxy-2-methoxypropoxy]-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane
• CAS: 180714-42-5
• 化学式: C₄₇H₇₀O₇
• 分子量: 747.069
• InChiKey: OMGCBLJWRPHRTA-JHPAFTAUSA-N

物化性质

• 沸点：
  772.1±60.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  54
• 可旋转键数：
  31
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,6R)-6-[(2R)-3-hexadecoxy-2-methoxypropoxy]-3,4-bis(phenylmethoxy)-2-(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,4R,6R)-6-((R)-3-(hexadecyloxy)-2-methoxypropoxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-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：

  (2R,3R,4R,5R,6R)-2-[(2R)-3-hexadecoxy-2-methoxypropoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol 在 咪唑 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 甲苯 为溶剂， 生成 (2R,3S,4R,6R)-6-[(2R)-3-hexadecoxy-2-methoxypropoxy]-3,4-bis(phenylmethoxy)-2-(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

• Novel Bicylic Donors for the Synthesis of 2-Deoxy-β-Glycosides
  作者：Richard W. Franck、Cecilia H. Marzabadi

  DOI：10.1021/jo971934h

  日期：1998.4.1

  Novel bicyclic glycosyl donors have been prepared by the cycloaddition reaction of glycals with 3-thiono-2,4-pentanedione 17 followed by methylenation of the resulting ketone. Treatment of the heterocyclic donors with triflic acid in the presence of a variety of alcohol accepters leads to the formation of beta-glycosides in good yields and with excellent stereoselectivities. Desulfurization of the C-2 carbon-sulfur bonds gives the corresponding 2-deoxy-beta-glycosides. This method has been extended to the synthesis of glycosidic linkages found in the aureolic acid antibiotics. Tetra-N-butylammonium triflate proved to be a useful additive in these glycosylation reactions, suggesting an important role for triflate anion in stabilizing intermediates which are formed.
• A novel donor for the synthesis of 2-deoxy-β-glycosides
  作者：Cecilia H. Marzabadi、Richard W. Franck

  DOI：10.1039/cc9960002651

  日期：——

  Vinyl glycoside 2, available in two steps from tribenzyl glucal, is found to be an excellent glycosyl donor for the synthesis of 2-deoxy-beta-glycosides.
• 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.