3,4,5,7-tetra-O-benzyl-α-D-manno-hept-2-ulopyranose | 388570-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,5,7-tetra-O-benzyl-α-D-manno-hept-2-ulopyranose
• 英文别名: 3,4,5,7-tetra-O-benzyl-α-D-glycero-D-lyxo-hept-2-ulopyranose；(2S,3S,4S,5R,6R)-2-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• CAS: 388570-21-6
• 化学式: C₃₅H₃₈O₇
• 分子量: 570.683
• InChiKey: WGFUUMQJBZIOKC-VABIIVNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-benzyl-α-D-manno-hept-2-ulopyranose 在 palladium dihydroxide 氢气 、 potassium trifluoromethansulfonate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 α-D-manno-hept-2-ulopyranose β-D-manno-hept-2'-ulopyranose 1,2':2,1'-dianhydride
  参考文献：
  名称：

  Stereoselective synthesis and structure elucidation of spiro-ketodisaccharides

  摘要：

  Cycloglycosylation of 3,4,5,7-tetra-O-benzyl-alpha -D-hept-2-ulopyranoses (2a-c) was carried out stereoselectively under the catalysis of Lewis acid to afford two spiro-cyclodisaccharides 3a-c and 4a-c in good yields. The reaction provided the kinetic products 3a-c or the thermodynamic products 4a-c as the predominant products under different conditions, respectively. The unprotected disaccharides 5a-c and 6a-c and the acetylated derivatives 7a-c and 5a-c were prepared by catalytic hydrogenation and followed by acetylation. The structures of compounds 4a-c, 6a-c and 8a-c were confirmed to be alpha,beta -anomeric configuration with chair-chair-chair forin for the tri-cycles based on the X-ray crystallographic analysis of 6a-c. The alpha,alpha -anomeric configurations of compounds 3a-c, 5a-c and 7a-c were determined based on the measurements of the three bond coupling constants (3)J(C,H) between the C-1 and the H-3 of 7a-c. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00775-x
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone 在 potassium osmate(VI) dihydrate 、 水 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 96.0h， 生成 3,4,5,7-tetra-O-benzyl-α-D-manno-hept-2-ulopyranose
  参考文献：
  名称：

  Highly Efficient Synthesis of Ketoheptoses

  摘要：

  A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.

  DOI：

  10.1021/ol2012764

文献信息

• Mannose derivatives useful for treating pathologies associated with adherent E. coli
  申请人：ENTEROME

  公开号：US10543223B2

  公开（公告）日：2020-01-28

  The present invention relates to mannose derivatives of formula (I): wherein R1 represents H, CO—(C1-C6)-alkyl or CO-alkylaryl, Y represents a single bond, CH2, O, NR3, S, A represents O, NH or S, X represents H and X′ represents OH or X and X′ taken together with the carbon atom bearing them form a CO group, R2 represents H, a linear or branched (C1-C6)-alkyl or CF3, R3 represents H, a C1-C6 alkyl, a CO—(C1-C6)-alkyl, CF3 or COCF3, and R is as described in claim 1. The mannose derivatives of formulae (I) are useful for treating pathologies associated with the presence of adherent Escherichia coli (AEC), in particular inflammatory bowel diseases (IBD), such as Crohn's disease and ulcerative colitis; a urinary tract infection, in particular painful bladder syndrome and cystitis, more particularly interstitial cystitis; irritable bowel syndrome; metabolic diseases such as metabolic obesity, diabetes, hypercholesterolemia; autoimmune inflammatory diseases; and colorectal cancer, in particular colon cancer.

  本发明涉及式 (I) 的甘露糖衍生物： 其中 R1 代表 H、CO-(C1-C6)-烷基或 CO-烷基芳基、 Y 代表单键、CH2、O、NR3、S、 A 代表 O、NH 或 S、 X 代表 H 和 X′ 代表 OH 或 X 和 X′ 与含有它们的碳原子一起构成 CO 基团、 R2 代表 H、直链或支链（C1-C6）-烷基或 CF3、 R3 代表 H、C1-C6 烷基、CO-(C1-C6)-烷基、CF3 或 COCF3，以及 R 如权利要求 1 所述。 式（I）的甘露糖衍生物可用于治疗与粘附性大肠杆菌（AEC）的存在有关的病症，特别是炎症性肠病（IBD），如克罗恩病和溃疡性结肠炎；泌尿道感染，特别是膀胱疼痛综合征和膀胱炎，尤其是间质性膀胱炎；肠易激综合征；代谢性疾病，如代谢性肥胖、糖尿病、高胆固醇血症；自身免疫性炎症；以及结肠直肠癌，特别是结肠癌。
• Regioselective synthesis and biological evaluation of spiro-sulfamidate glycosides from exo-glycals
  作者：Mahmoud Benltifa、Miklos De Kiss、Maria Isabel Garcia-Moreno、Carmen Ortiz Mellet、David Gueyrard、Anne Wadouachi

  DOI：10.1016/j.tetasy.2009.07.012

  日期：2009.8

  We report the synthesis of spiro-sulfamidate glycosides from exo-glycals. This route is regioselective and furnishes an original class of spiro-hydantoin glycoside analogues. A biological evaluation of this family on a range of glycosidases shows that these compounds are weak but very selective inhibitors of a-glucosidase and amyloglucosidase. (c) 2009 Elsevier Ltd. All rights reserved.
• MANNOSE DERIVATIVES USEFUL FOR TREATING PATHOLOGIES ASSOCIATED WITH ADHERENT E. COLI
  申请人：Enterome

  公开号：EP3331893B1

  公开（公告）日：2019-05-22
• Highly Efficient Synthesis of Ketoheptoses
  作者：Daniel Waschke、Julian Thimm、Joachim Thiem

  DOI：10.1021/ol2012764

  日期：2011.7.15

  A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.
• Stereoselective synthesis and structure elucidation of spiro-ketodisaccharides
  作者：Xiaoliu Li、Hideyo Takahashi、Hiro Ohtake、Moto Shiro、Shiro Ikegami

  DOI：10.1016/s0040-4020(01)00775-x

  日期：2001.9

  Cycloglycosylation of 3,4,5,7-tetra-O-benzyl-alpha -D-hept-2-ulopyranoses (2a-c) was carried out stereoselectively under the catalysis of Lewis acid to afford two spiro-cyclodisaccharides 3a-c and 4a-c in good yields. The reaction provided the kinetic products 3a-c or the thermodynamic products 4a-c as the predominant products under different conditions, respectively. The unprotected disaccharides 5a-c and 6a-c and the acetylated derivatives 7a-c and 5a-c were prepared by catalytic hydrogenation and followed by acetylation. The structures of compounds 4a-c, 6a-c and 8a-c were confirmed to be alpha,beta -anomeric configuration with chair-chair-chair forin for the tri-cycles based on the X-ray crystallographic analysis of 6a-c. The alpha,alpha -anomeric configurations of compounds 3a-c, 5a-c and 7a-c were determined based on the measurements of the three bond coupling constants (3)J(C,H) between the C-1 and the H-3 of 7a-c. (C) 2001 Elsevier Science Ltd. All rights reserved.