benzyl 6-deoxy-α-D-glucopyranoside | 114298-06-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-deoxy-α-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-methyl-6-phenylmethoxyoxane-3,4,5-triol
• CAS: 114298-06-5
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: UHQDDNIUJBFOEL-ZMHPAJMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  正丁酸2,2,2-三氟乙酯 、 benzyl 6-deoxy-α-D-glucopyranoside 在 subtilisin 作用下， 以 丙酮 为溶剂， 生成 benzyl 3-O-butanoyl-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2

  摘要：

  Subtilisin-catalyzed esterification of several enantiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01217-4
• 作为产物：
  描述：

  benzyl 6-O-p-toluene-sulfonyl-α-D-glucopyranoside 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 benzyl 6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2

  摘要：

  Subtilisin-catalyzed esterification of several enantiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01217-4

文献信息

• Partially Benzylated Derivatives of 6-Deoxy-D-glucose
  作者：Shinkiti Koto、Naohiko Morishima、Yoko Mori、Hitoshi Tanaka、Seiichi Hayashi、Yumi Iwai、Shonosuke Zen

  DOI：10.1246/bcsj.60.2301

  日期：1987.6

  Several partially benzylated derivatives of 6-deoxy-d-glucose (d-quinovose) were synthesized from appropriate di-O-benzyl-d-glucosides whose primary hydroxyl group is unprotected, via unimolar tosylation and subsequent reduction with LiAlH4.

  通过单摩尔数量的甲苯磺酰化反应和随后的LiAlH4还原反应，从适当的二-O-苄基-d-葡糖苷（其伯羟基未保护）合成了6-脱氧-d-葡萄糖（d-黄花草糖）的几种部分苄基化衍生物。
• On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2
  作者：Bruno Danieli、Francesco Peri、Gabriella Roda、Giacomo Carrea、Sergio Riva

  DOI：10.1016/s0040-4020(98)01217-4

  日期：1999.2

  Subtilisin-catalyzed esterification of several enantiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated. (C) 1999 Elsevier Science Ltd. All rights reserved.