methyl 2,3,4-tri-O-benzyl-α-D-glucopyranuronate | 75336-65-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-α-D-glucopyranuronate
• 英文别名: Methyl (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-hydroxytetrahydro-2H-pyran-2-carboxylate；methyl (2S,3S,4S,5R,6S)-6-hydroxy-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate
• CAS: 75336-65-1
• 化学式: C₂₈H₃₀O₇
• 分子量: 478.542
• InChiKey: NKKRXSRPNADUQE-HIBXFOCJSA-N

物化性质

• 沸点：
  602.8±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-glucopyranuronate 在 silver perchlorate 、 三溴化磷 、 乙腈 作用下， 生成 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselective glycosidations of uronic acids

  摘要：

  DOI：

  10.1016/s0040-4039(00)92735-7
• 作为产物：
  描述：

  乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 吡啶 、 盐酸 、 sodium acetate 、 氰化汞 、 溶剂黄146 、 六甲基二硅氮烷 、 potassium iodide 、 mercury dibromide 、 palladium dichloride 、 silver(l) oxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.5h， 生成 methyl 2,3,4-tri-O-benzyl-α-D-glucopyranuronate
  参考文献：
  名称：

  Comparison of Several Glucuronate Glycosyl Donors

  摘要：

  Methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-alpha-D-glucopyranuronate (12), methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-alpha-D-glucopyranuronate (14), methyl 2-O-acetyl-3,4-di-O-benzyl-alpha-D-glucopyranuronate bromide (15), methyl (2-O-acetyl-3,4-di-O-benzyl-alpha-D-glucopyranosyl)uronate trichloroacetimidate (17), and methyl (2,3,4-tri-O-benzyl-alpha/beta-D-glucopyranosyl)uronate trichloroacetimidate (30) were synthesized and used as glycosyl donors. Glycosylation reactions of 12 with (5-R)-2,3,4,5-tetrahydro-5-trityloxymethyl-2-furanone (32) and 14,15,17 with the corresponding (5-R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (31) provided the exclusively beta-linked glucuronide 33 in 69%, 28%, 45%, and 71% yield, respectively. The coupling of donor 30 with acceptor 31 furnished the glucuronated lactone 35 in 70% yield with a surprisingly high content (20%) of the undesired alpha-linked sugar residue. The structure of 33 was proved by NMR and X-ray diffraction studies. In a model reaction a complete deprotection procedure of the glucuronic acid lactone conjugation was demonstrated.

  DOI：

  10.1081/car-120026603

文献信息

• An extremely mild and stereocontrolled construction of 1,2-trans-β-glycosidic linkages capitalizing on benzyl-protected glycopyranosyl diethyl phosphites as glycosyl donors
  作者：Shun-ichi Hashimoto、Kazuhiro Umeo、Ai Sano、Nobuhide Watanabe、Makoto Nakajima、Shiro Ikegami

  DOI：10.1016/0040-4039(95)00263-c

  日期：1995.3

  neighboring group participation has been developed by using benzyl-protected glycopyranosyl diethyl phosphites as glycosyl donors and boron trifluoride etherate as a promoter. The present method exhibits the highest level of 1,2-trans-β-selectivity known to date for glycosidations with a non-participating group on O-2.

  已经通过使用苄基保护的亚磷酸吡喃葡萄糖基二乙基亚磷酸酯作为糖基供体和三氟化硼醚化物作为促进剂，开发了没有相邻基团参与的高度立体控制的1,2-反式-β-糖苷化反应。本方法展现出迄今已知的对于O-2上具有非参与基团的糖苷化的最高水平的1，2-反式-β-选择性。
• Comparison of Several Glucuronate Glycosyl Donors
  作者：Anahit Pews‐Davtyan、Alexander Pirojan、Izabella Shaljyan、Aida A. Awetissjan、Helmut Reinke、Christian Vogel

  DOI：10.1081/car-120026603

  日期：2003.12.31

  Methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-alpha-D-glucopyranuronate (12), methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]-alpha-D-glucopyranuronate (14), methyl 2-O-acetyl-3,4-di-O-benzyl-alpha-D-glucopyranuronate bromide (15), methyl (2-O-acetyl-3,4-di-O-benzyl-alpha-D-glucopyranosyl)uronate trichloroacetimidate (17), and methyl (2,3,4-tri-O-benzyl-alpha/beta-D-glucopyranosyl)uronate trichloroacetimidate (30) were synthesized and used as glycosyl donors. Glycosylation reactions of 12 with (5-R)-2,3,4,5-tetrahydro-5-trityloxymethyl-2-furanone (32) and 14,15,17 with the corresponding (5-R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (31) provided the exclusively beta-linked glucuronide 33 in 69%, 28%, 45%, and 71% yield, respectively. The coupling of donor 30 with acceptor 31 furnished the glucuronated lactone 35 in 70% yield with a surprisingly high content (20%) of the undesired alpha-linked sugar residue. The structure of 33 was proved by NMR and X-ray diffraction studies. In a model reaction a complete deprotection procedure of the glucuronic acid lactone conjugation was demonstrated.
• Stereoselective glycosidations of uronic acids
  作者：Richard R. Schmidt、Ernst Rücker

  DOI：10.1016/s0040-4039(00)92735-7

  日期：——