1-O-allyl-2,3,4-tri-O-benzyl-β-D-glucose 6-O-tosylate | 267900-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-allyl-2,3,4-tri-O-benzyl-β-D-glucose 6-O-tosylate
• 英文别名: 2,3,4-tri-O-benzyl-1-0-(2-propenyl)-6-0-(4-tolylsulfonyl)-β-D-glucose；[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-prop-2-enoxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 267900-41-4
• 化学式: C₃₇H₄₀O₈S
• 分子量: 644.786
• InChiKey: MGEYVZSIQLPAQU-KHKVHWIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-O-allyl-2,3,4-tri-O-benzyl-β-D-glucose 6-O-tosylate 在 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 叔丁醇 为溶剂， 生成 Octadecanoic acid 3-((2R,3R,4S,5S,6S)-6-acetylsulfanylmethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-2-hydroxy-propyl ester
  参考文献：
  名称：

  Synthesis of an immunosuppressant SQAG9 and determination of the binding peptide by T7 phage display

  摘要：

  SQAG9, a new class of immunosuppressive sulfoquinovosylacylglycerol, and its biotinylated derivatives have been synthesized. A T7 Phage library, composed of random cDNA fragments from Drosophila melanogaster, displayed a possible binding peptide of 14 amino acids. The immobilized synthetic peptide on a sensor chip showed a dissociation constant of K-D = 1.5 x 10(-6) against SQAG9 in a surface plasmon resonance experiment. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.085
• 作为产物：
  描述：

  allyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 、 对甲苯磺酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以89.8%的产率得到1-O-allyl-2,3,4-tri-O-benzyl-β-D-glucose 6-O-tosylate
  参考文献：
  名称：

  Synthesis of an immunosuppressant SQAG9 and determination of the binding peptide by T7 phage display

  摘要：

  SQAG9, a new class of immunosuppressive sulfoquinovosylacylglycerol, and its biotinylated derivatives have been synthesized. A T7 Phage library, composed of random cDNA fragments from Drosophila melanogaster, displayed a possible binding peptide of 14 amino acids. The immobilized synthetic peptide on a sensor chip showed a dissociation constant of K-D = 1.5 x 10(-6) against SQAG9 in a surface plasmon resonance experiment. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.085

文献信息

• Novel sulfoquinovosylacylglycerol derivative, and use thereof as medicaments
  申请人：TOYO SUISAN KAISHA, LTD.

  公开号：US20020052327A1

  公开（公告）日：2002-05-02

  A method for immunosuppression in a subject comprising administering to the subject in need thereof, a pharmaceutically effective amount of at least one sulfoquinovosylacylglycerol derivative represented by General formula (1-1): 1 wherein R 101 represents an acyl residue of a higher fatty acid, and R 102 represents a hydrogen atom or an acyl residue of a higher fatty acid; and a pharmaceutically acceptable salt thereof. Of the sulfoquinovosylacylglycerol derivatives, &bgr;-sulfoquinovosylacylglycerols are novel compounds. The present invention also relates to pharmaceutical composition comprising a pharmaceutically effective amount of the &bgr;-sulfoquinovosylacylglycerols and/or its pharmaceutically acceptable salt; and a pharmaceutically acceptable excipient. The pharmaceutical composition may be used as an immunosuppressive agent, anticancer agent and DNA polymerase &agr; inhibitor.

  一种在需要免疫抑制的主体中进行的免疫抑制方法，包括向该主体给药至少一种由通用公式（1-1）表示的磺酰基糖醇基甘油酯衍生物的药物有效量： 1 其中R 101 代表一种较高脂肪酸的酰基残基，R 102 代表一个氢原子或一个较高脂肪酸的酰基残基；以及一种药物可接受的盐。在磺酰基糖醇基甘油酯衍生物中，β-磺酰基糖醇基甘油酯是新颖的化合物。本发明还涉及包含β-磺酰基糖醇基甘油酯和/或其药物可接受的盐的药物有效量的药物组合物；以及一种药物可接受的辅料。该药物组合物可作为免疫抑制剂、抗癌剂和DNA聚合酶α抑制剂使用。
• Method of treating cancer
  申请人：TOYO SUISAN KAISHA, LTD.

  公开号：US20020173471A1

  公开（公告）日：2002-11-21

  An anticancer drug includes a compound represented by Formula (1): 1 where R 101 represents an acyl moiety of a saturated higher fatty acid, and R 102 represents a hydrogen atom or an acyl moiety of a saturated higher fatty acid, and/or a pharmaceutically acceptable salt thereof.

  抗癌药物包括由式（1）代表的化合物： 1 其中 R 101 代表饱和高级脂肪酸的酰基，R 102 代表氢原子或饱和高级脂肪酸的酰基，和/或其药学上可接受的盐。
• US6395886B1
  申请人：——

  公开号：US6395886B1

  公开（公告）日：2002-05-28
• US6444795B1
  申请人：——

  公开号：US6444795B1

  公开（公告）日：2002-09-03
• US6518248B1
  申请人：——

  公开号：US6518248B1

  公开（公告）日：2003-02-11