methyl 2-deoxy-2-fluoro-α,β-D-glucopyranoside | 128572-49-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-deoxy-2-fluoro-α,β-D-glucopyranoside
• 英文别名: Methyl 2-deoxy-2-fluoro-D-glucopyranoside；methyl-2-deoxy-2-fluoro-D-glucopyranoside；(2R,3S,4S,5R)-5-fluoro-2-(hydroxymethyl)-6-methoxyoxane-3,4-diol
• CAS: 128572-49-6
• 化学式: C₇H₁₃FO₅
• 分子量: 196.176
• InChiKey: CRIUOMMBWCCBCQ-YDEIVXIUSA-N

物化性质

• 沸点：
  352.7±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-2-fluoro-α,β-D-glucopyranoside 在 对甲苯磺酸 sodium tetrahydroborate 、 重铬酸吡啶 、 3 Angstroem MS 、 三氟乙酸吡啶 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 methyl 4,6-O-benzylidene-2-dexoxy-2-fluoro-α-and β-D-allopyranoside
  参考文献：
  名称：

  Anthracycline glycosides of 2,6-dideoxy-2-fluoro-α-l-talopyranose

  摘要：

  The methyl beta-glycoside of the title sugar, obtained from 2-deoxy-2-fluoro-beta-D-glucopyranose tetraacetate by a sequence with detailed characterization of all intermediates, was converted by acetolysis-bromination into 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide, coupling of which with (7S,9S)-4-demethoxydaunomycinone afforded the 3,4-diacetate of 4-demethoxy-9-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl) daunomycin one (19). The antitumor-active 19 was converted by way of its 14-bromo derivative into the 14-hydroxy analogue, the antitumor-active 4-d emethoxyadriamycin one glycoside 21. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.024
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose 在 Dowex 50W X 8 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以45%的产率得到methyl 2-deoxy-2-fluoro-α,β-D-glucopyranoside
  参考文献：
  名称：

  OLIGOSACCHARIDE DERIVATIVE

  摘要：

  公开号：

  EP1589023B1

文献信息

• L-talopyranoside derivatives and process for the preparation of same
  申请人：Dong-A Pharmaceutical Co., Ltd.

  公开号：US05374746A1

  公开（公告）日：1994-12-20

  The present invention relates to a L-talopyranoside derivative of the formula (I): ##STR1## wherein, A is hydrogen atom, a lower alkyl group having 1 to 5 carbon atoms, or a hydroxyl-protecting group; B.sub.1 and B.sub.2, the same or different from each other, are independently hydrogen atom or a hydroxyl-protecting group; R.sub.1 and R.sub.2 may form a alkylene group with a carbon atom of 5-position of the sugar skeleton, or one of them is hydrogen atom and the other is CH.sub.2 X wherein, X is hydrogen, or a protected or un-protected hydroxyl group. Provided that, the following compounds are excepted: ##STR2## wherein, B.sub.1 and B.sub.2 are independently hydrogen atom or acetyl. L-talopyronoside derivatives of the present invention is a very useful intermediate for the synthesis of anthracycline antibiotics having an antitumor activity. The process according to the invention has an advantage of significant reduction in the production cost and therefore expected to be very useful for the preparation of anthracycline antibiotics in an industrial scale.

  本发明涉及一种L-塔洛吡喃糖苷衍生物，其结构式如式(I)所示：##STR1##其中，A为氢原子、含有1至5个碳原子的低级烷基或羟基保护基；B1和B2彼此相同或不同，各自独立地为氢原子或羟基保护基；R1和R2可以与糖骨架5位上的碳原子形成亚烷基，或者其中之一为氢原子，另一个为CH2X，其中X为氢，或保护或未保护的羟基。但以下化合物除外：##STR2##其中，B1和B2各自独立地为氢原子或乙酰基。本发明的L-塔洛吡喃糖苷衍生物是合成具有抗肿瘤活性的蒽环类抗生素的非常有用的中间体。根据本发明的工艺具有显著降低生产成本的优点，因此预计在工业规模制备蒽环类抗生素方面非常有用。
• Oligosaccharide derivative
  申请人：Honda Takeshi

  公开号：US20060025350A1

  公开（公告）日：2006-02-02

  Compounds having the formula (I): wherein A represents a group such as a cyclic group, R 1 and R 2 represent groups such as alkyl groups or hydroxymethyl groups, and n represents 1 or 2, or pharmacologically acceptable salts thereof or pharmacologically acceptable esters thereof have superior activity and stability, and are useful for the treatment and/or prevention of diabetes mellitus, or the like.

  具有化学式（I）的化合物：其中A代表环状基团，R1和R2代表烷基或羟甲基等基团，n代表1或2，或其药学上可接受的盐或酯具有卓越的活性和稳定性，并且可用于治疗和/或预防糖尿病等疾病。
• Medicinal Composition Containing Diabeted Remedy
  申请人：Izumi Masanori

  公开号：US20080039367A1

  公开（公告）日：2008-02-14

  A pharmaceutical composition effective for the prophylaxis and treatment of diabetes is provided. This pharmaceutical composition comprises the combination of an α-amylase inhibitor selected from a compound represented by the following general formula (I): [wherein A represents, for example, a cyclic group, etc. R 1 and R 2 represent an alkyl group, hydroxymethyl group, etc., and n represents 1 or 2], or a pharmacologically acceptable salt or ester thereof, and at least one type of drug selected from an insulin sensitizer, an insulin secretagogue, a biguanide drug, an insulin preparation and a DPP-IV inhibitor.

  提供一种用于预防和治疗糖尿病的药物组合物。该药物组合物包括以下通用式（I）所表示的化合物中选择的α-淀粉酶抑制剂：[其中A代表环状基团等，R1和R2代表烷基、羟甲基基团等，n代表1或2]，或其药理学上可接受的盐或酯，以及选择自胰岛素增敏剂、胰岛素分泌促进剂、双胍类药物、胰岛素制剂和DPP-IV抑制剂中的至少一种药物。
• Oligosaccharide Derivative
  申请人：Honda Takeshi

  公开号：US20080194495A1

  公开（公告）日：2008-08-14

  Compounds having the formula (I): wherein A represents a group such as a cyclic group, R 1 and R 2 represent groups such as alkyl groups or hydroxymethyl groups, and n represents 1 or 2, or pharmacologically acceptable salts thereof or pharmacologically acceptable esters thereof have superior activity and stability, and are useful for the treatment and/or prevention of diabetes mellitus, or the like.

  具有式(I)的化合物：其中A表示环状基团，R1和R2表示烷基或羟甲基等基团，n表示1或2，或其药学上可接受的盐或酯，在活性和稳定性方面具有优越性，可用于治疗和/或预防糖尿病等疾病。
• Medicinal composition containing diabetes remedy
  申请人：Sankyo Company, Limited

  公开号：US07943584B2

  公开（公告）日：2011-05-17

  A pharmaceutical composition effective for the prophylaxis and treatment of diabetes is provided. This pharmaceutical composition comprises the combination of an α-amylase inhibitor selected from a compound represented by the following general formula (I): [wherein A represents, for example, a cyclic group, etc. R1 and R2 represent an alkyl group, hydroxymethyl group, etc., and n represents 1 or 2], or a pharmacologically acceptable salt or ester thereof, and at least one type of drug selected from an insulin sensitizer, an insulin secretagogue, a biguanide drug, an insulin preparation and a DPP-IV inhibitor.

  提供了一种对糖尿病预防和治疗有效的药物组合物。该药物组合物包括选自以下通式（I）所表示的化合物中的α-淀粉酶抑制剂[其中A代表环状基团等，R1和R2代表烷基基团，羟甲基基团等，n代表1或2]，或其药理学上可接受的盐或酯，以及至少一种从胰岛素敏化剂、胰岛素分泌剂、双胍类药物、胰岛素制剂和DPP-IV抑制剂中选择的药物。