benzyl 6-bromo-2,6-dideoxy-α-D-glucopyranoside | 145295-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-bromo-2,6-dideoxy-α-D-glucopyranoside
• 英文别名: (2S,3S,4R,6S)-2-(bromomethyl)-6-phenylmethoxyoxane-3,4-diol
• CAS: 145295-38-1
• 化学式: C₁₃H₁₇BrO₄
• 分子量: 317.18
• InChiKey: CLACWNXQSFKVJW-NDBYEHHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 6-bromo-2,6-dideoxy-α-D-glucopyranoside 在 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 Benzyl 2,6-Dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Unusual stereoselectivity in sialic acid aldolase-catalyzed aldol condensations: synthesis of both enantiomers of high-carbon monosaccharides

  摘要：

  An inversion of stereoselectivity in aldol condensations catalyzed by sialic acid aldolase (from Escherichia coli, Shinko American Inc.) was observed when L-mannose, 6-deoxy-L-mannose, L-talose, 2-deoxy-L-glucose, 2-deoxy-L-rhamnose, N-acetyl-L-mannosamine, D-gulose, D-arabinose, and 2-azido-2-deoxy-L-mannose were used as acceptor substrates. In all substrates tested, except the last three, a complete inversion of stereoselectivity was observed; i.e., the C-nucleophile of pyruvate attacks the re face of the acceptor carbonyl instead of the si face as in the normal case for the enantiomeric substrates. Examination of the product distribution during the course of enzymatic reactions indicates that the stereoselectivity is thermodynamically controlled in nature; i.e., attack on the re face would take place if the resulting product would be more stable than the one from the si face attack. Both enantiomers of several high-carbon monosaccharides are now accessible via the aldolase reactions. A new practical procedure has also been developed for the preparation of the aldolase products where unreacted pyruvate (usually used in 7-fold excess to drive the reaction) is decomposed with pyruvate decarboxylase to simplify product isolation.

  DOI：

  10.1021/ja00052a008
• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 吡啶 、 四溴化碳 、 Dowex 50W-X₈ (H⁺ form) 、 三苯基膦 作用下， 反应 34.0h， 生成 benzyl 6-bromo-2,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Unusual stereoselectivity in sialic acid aldolase-catalyzed aldol condensations: synthesis of both enantiomers of high-carbon monosaccharides

  摘要：

  An inversion of stereoselectivity in aldol condensations catalyzed by sialic acid aldolase (from Escherichia coli, Shinko American Inc.) was observed when L-mannose, 6-deoxy-L-mannose, L-talose, 2-deoxy-L-glucose, 2-deoxy-L-rhamnose, N-acetyl-L-mannosamine, D-gulose, D-arabinose, and 2-azido-2-deoxy-L-mannose were used as acceptor substrates. In all substrates tested, except the last three, a complete inversion of stereoselectivity was observed; i.e., the C-nucleophile of pyruvate attacks the re face of the acceptor carbonyl instead of the si face as in the normal case for the enantiomeric substrates. Examination of the product distribution during the course of enzymatic reactions indicates that the stereoselectivity is thermodynamically controlled in nature; i.e., attack on the re face would take place if the resulting product would be more stable than the one from the si face attack. Both enantiomers of several high-carbon monosaccharides are now accessible via the aldolase reactions. A new practical procedure has also been developed for the preparation of the aldolase products where unreacted pyruvate (usually used in 7-fold excess to drive the reaction) is decomposed with pyruvate decarboxylase to simplify product isolation.

  DOI：

  10.1021/ja00052a008

文献信息

• US6353095B1
  申请人：——

  公开号：US6353095B1

  公开（公告）日：2002-03-05
• [EN] KETOALDONIC ACIDS HAVING FORMED STEREOGENIC CENTERS OF R CONFIGURATION: METHODS AND COMPOSITIONS
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：WO1993006227A1

  公开（公告）日：1993-04-01

  (EN) The present invention provides a ketoaldonic acid such as an octulosonic or nonulosonic acid having formed stereogenic center of R configuration, as well as methods of synthesizing the same.(FR) L'invention se rapporte à un acide cétoaldonique tel qu'un acide octulosonique ou nonulosonique ayant un centre stéréogénique formé présentant une configuration en R, ainsi qu'à des procédés de synthèse d'un tel acide.
• Unusual stereoselectivity in sialic acid aldolase-catalyzed aldol condensations: synthesis of both enantiomers of high-carbon monosaccharides
  作者：Chun Hung Lin、Takeshi Sugai、Randall L. Halcomb、Yoshitaka Ichikawa、Chi Huey Wong

  DOI：10.1021/ja00052a008

  日期：1992.12

  An inversion of stereoselectivity in aldol condensations catalyzed by sialic acid aldolase (from Escherichia coli, Shinko American Inc.) was observed when L-mannose, 6-deoxy-L-mannose, L-talose, 2-deoxy-L-glucose, 2-deoxy-L-rhamnose, N-acetyl-L-mannosamine, D-gulose, D-arabinose, and 2-azido-2-deoxy-L-mannose were used as acceptor substrates. In all substrates tested, except the last three, a complete inversion of stereoselectivity was observed; i.e., the C-nucleophile of pyruvate attacks the re face of the acceptor carbonyl instead of the si face as in the normal case for the enantiomeric substrates. Examination of the product distribution during the course of enzymatic reactions indicates that the stereoselectivity is thermodynamically controlled in nature; i.e., attack on the re face would take place if the resulting product would be more stable than the one from the si face attack. Both enantiomers of several high-carbon monosaccharides are now accessible via the aldolase reactions. A new practical procedure has also been developed for the preparation of the aldolase products where unreacted pyruvate (usually used in 7-fold excess to drive the reaction) is decomposed with pyruvate decarboxylase to simplify product isolation.