1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside | 265312-92-3

• 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-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside
• 英文别名: 2,3,4-tri-O-(t-butyldimethylsilyl)-1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-α-D-glucose；TBDMS(-2)[TBDMS(-3)][TBDMS(-4)][Tos(-6)]Glc(a)-O-allyl；[(2R,3R,4S,5R,6S)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-6-prop-2-enoxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 265312-92-3
• 化学式: C₃₄H₆₄O₈SSi₃
• 分子量: 717.2
• InChiKey: FYFMWZVCWPQWTA-SAEUYMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 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-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 57.0h， 生成 3-O-[2,3,4-tri-O-(tert-butyldimethylsilyl)-6-deoxy-6-thioacetyl-α-D-glucopyranosyl]-1-O-oleoyl-glycerol
  参考文献：
  名称：

  Synthesis of sulfoquinovosylacylglycerols, inhibitors of Eukaryotic DNA Polymerase α and β

  摘要：

  Sulfoquinovosyldiacylglycerols (SQDGs) and sulfoquinovosylmonoacylglycerols (SQMGs), bearing diverse fatty acids, were synthesized from D-glucose, and were examined for enzymatic inhibitions of DNA polymerase alpha and beta. These results indicated that the carbon numbers of the fatty acids were highly related to the activities, at least in vitro, of eukaryotic DNA polymerase inhibition. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00252-2
• 作为产物：
  描述：

  2-PROPENYL4,6-O-BENZYLIDENE-Α-D-GLUCOPYRANOSIDE2-丙烯基4,6-O-亚苄基-Α-D-吡喃葡萄糖苷 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 33.0h， 生成 1-O-allyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside
  参考文献：
  名称：

  COMPOUND RETAINED IN TUMOR

  摘要：

  提供了一种新型化合物，该化合物特异地存在于肿瘤中，提供了一种使其在肿瘤中存在的方法，以及一种利用它进行肿瘤检测、诊断和治疗的方法。本发明涉及一种由化学式（I）表示的化合物，其中R是与氢结合的阴离子基团，R1是OH、OCOH、OCO（CH2）hCH3或作用基团，h为0或更多的整数，R2是H、OH、OCOH、OCO（CH2）iCH3或作用基团，i为0或更多的整数，R3是OH、SO3H或作用基团，R4是OH、SO3H或作用基团，R5是OH、SO3H或作用基团，R1、R2、R3、R4和R5中至少一个含有作用基团，或其药学上可接受的盐。

  公开号：

  EP2388264A1

文献信息

• Medicament containing a sulfopyranosylacylglycerol derivative
  申请人：TOYO SUISAN KAISHA, LTD.

  公开号：US20020028776A1

  公开（公告）日：2002-03-07

  A medicament containing at least one compound selected from the group consisting of compounds represented by General formula (1): 1 wherein R 101 represents an acyl residue of an unsaturated higher fatty acid, and R 102 represents a hydrogen atom or an acyl residue of an unsaturated higher fatty acid, and pharmaceutically acceptable salts thereof, as an active ingredient.

  包含至少一种从以下组中选择的化合物的药物：由通用公式(1)表示的化合物组1其中，R101代表不饱和高级脂肪酸的酰基残基，R102代表氢原子或不饱和高级脂肪酸的酰基残基，以及药用可接受的盐作为有效成分。
• 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。
• Sulfoquinovosylacylglycerol derivative, and use thereof as medicaments
  申请人：Toyo Suisan Kaisha, Ltd.

  公开号：US06518410B2

  公开（公告）日：2003-02-11

  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): wherein R101 represents an acyl residue of a higher fatty acid, and R102 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.

  一种在受试者中实现免疫抑制的方法，包括向需要该方法的受试者施用至少一种由通用公式（1-1）表示的磺酰基糖醇基甘油衍生物的药用有效量： 其中R101代表一个较高脂肪酸的酰基残基，R102代表一个氢原子或一个较高脂肪酸的酰基残基；以及药用可接受的盐。在磺酰基糖醇基甘油衍生物中，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/或其药用可接受的盐的药用有效量的药物组合物；以及药用可接受的辅料。该药物组合物可以用作免疫抑制剂、抗癌剂和DNA聚合酶α抑制剂。
• COMPOUND RETAINED IN TUMOR
  申请人：Toyo Suisan Kaisha, Ltd.

  公开号：EP2388264A1

  公开（公告）日：2011-11-23

  A novel compound which specifically resides in a tumor, a method for allowing it to reside in a tumor, and a method for detecting, diagnosing, and treating tumor with use thereof are provided. The present invention relates to a compound represented by chemical formula (I) wherein R is an anionic group binding to hydrogen, R1 is OH, OCOH, OCO(CH2)hCH3, or an acting group, h being an integer of 0 or more, R2 is H, OH, OCOH, OCO(CH2)iCH3, or an acting group, i being an integer of 0 or more, R3 is OH, SO3H, or an acting group, R4 is OH, SO3H, or an acting group, and R5 is OH, SO3H, or an acting group, at least one of R1, R2, R3, R4, and R5 containing an acting group, or pharmaceutically acceptable salts thereof.

  提供了一种新型化合物，该化合物特异地存在于肿瘤中，提供了一种使其在肿瘤中存在的方法，以及一种利用它进行肿瘤检测、诊断和治疗的方法。本发明涉及一种由化学式（I）表示的化合物，其中R是与氢结合的阴离子基团，R1是OH、OCOH、OCO（CH2）hCH3或作用基团，h为0或更多的整数，R2是H、OH、OCOH、OCO（CH2）iCH3或作用基团，i为0或更多的整数，R3是OH、SO3H或作用基团，R4是OH、SO3H或作用基团，R5是OH、SO3H或作用基团，R1、R2、R3、R4和R5中至少一个含有作用基团，或其药学上可接受的盐。
• Synthesis of sulfoquinovosylacylglycerols, inhibitors of Eukaryotic DNA Polymerase α and β
  作者：Shinya Hanashima、Yoshiyuki Mizushina、Takayuki Yamazaki、Keisuke Ohta、Syunya Takahashi、Hiroeki Sahara、Kengo Sakaguchi、Fumio Sugawara

  DOI：10.1016/s0968-0896(00)00252-2

  日期：2001.2

  Sulfoquinovosyldiacylglycerols (SQDGs) and sulfoquinovosylmonoacylglycerols (SQMGs), bearing diverse fatty acids, were synthesized from D-glucose, and were examined for enzymatic inhibitions of DNA polymerase alpha and beta. These results indicated that the carbon numbers of the fatty acids were highly related to the activities, at least in vitro, of eukaryotic DNA polymerase inhibition. (C) 2001 Elsevier Science Ltd. All rights reserved.