α-D-glucofurano<1,2-d>oxazolidin-2-one | 134040-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: α-D-glucofurano<1,2-d>oxazolidin-2-one
• 英文别名: 1-N,2-O-carbonyl-α-D-glucofuranosylamine；N,O²-carbonyl-β-D-glucofuranosylamine；N,O²-Carbonyl-β-D-glucofuranosylamin；(3aS,5R,6S,6aR)-5-[(1R)-1,2-dihydroxyethyl]-6-hydroxy-3a,5,6,6a-tetrahydro-3H-furo[2,3-d][1,3]oxazol-2-one
• CAS: 134040-39-4
• 化学式: C₇H₁₁NO₆
• 分子量: 205.167
• InChiKey: CPBONPURCYQKHB-RXRWUWDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-D-glucofurano<1,2-d>oxazolidin-2-one 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 74.83h， 生成 [(2R)-2-[(3aS,5R,6S,6aR)-6-(2,2-dimethylpropanoyloxy)-3-[(2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoyl]-2-oxo-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]oxazol-5-yl]-2-(2,2-dimethylpropanoyloxy)ethyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  New glyco-oxazolidin-2-ones as chiral auxiliaries in boron-mediated asymmetric aldol reactions

  摘要：

  Two new chiral glyco-oxazolidin-2-one auxiliaries based on D-glucose are described. Some N-acyl derivatives were synthesized and used in dialkylboron-mediated asymmetric aldol reactions. All reactions delivered as the major diastereomer those predicted by the Zimmerman-Traxler model and were separated by column chromatography and mostly isolated in moderate to good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00503-0
• 作为产物：
  描述：

  葡萄糖 在 盐酸 、 sodium hydroxide 、 双氧水 作用下， 生成 α-D-glucofurano<1,2-d>oxazolidin-2-one
  参考文献：
  名称：

  Zemplen et al., Chemische Berichte, 1936, vol. 69, p. 748,752

  摘要：

  DOI：

文献信息

• Transformation of aldoses into glycosylamine 1,2-(cyclic carbamates) (glyco-oxazolidin-2-ones) by reaction with potassium cyanate
  作者：József Kovács、István Pintér、Ursula Lendering、Peter Köll

  DOI：10.1016/0008-6215(91)80119-8

  日期：1991.3

  some hexoses with potassium cyanate in aqueous solutions, buffered with sodium dihydrogen phosphate or ammonium chloride, gave glycosylamine 1,2-(cyclic carbamates) glycofurano(or pyrano)[1,2-d]oxazolidin-2-ones}. Most of the products had furanoid structures, but d -mannose and d -lyxose gave preponderantly pyranose derivatives. Epimerisation at C-2 was observed in certain reactions. The products and

  摘要用磷酸氢二钠或氯化铵缓冲水溶液中的氰酸钾水溶液处理戊糖和一些己糖，得到糖胺1,2-（环氨基甲酸酯）糖呋喃诺（或吡喃）[1,2-d]恶唑烷-2-那些}。大多数产物具有呋喃样结构，但是d-甘露糖和d-lyxose主要产生吡喃糖衍生物。在某些反应中观察到C-2的差向异构。产物及其乙酰化衍生物通过1H-和13C-nmr光谱进行表征。
• Studies of the synthesis of 1,2-cis-(cyclic carbamates) of α-d-aldopyranosylamines
  作者：József Kovács、István Pintér、Gábor Tóth、Zoltán Györgydeák、Peter Köll

  DOI：10.1016/0008-6215(93)84206-l

  日期：1993.2

  derivatives were established by 1 H and 13 C NMR spectroscopy. 1- N ,3- O -Carbonyl-β- d -xylopyranosylamine ( 21 ) was obtained from β- d -xylopyranosyl azide when spontaneous rearrangement of the 1,2-(cyclic carbamate) 5 into 21 occurred in water.

  摘要α-d-吡喃葡萄糖基叠氮化物与三苯基膦和二氧化碳反应，生成1- N，2- O-羰基-α-d-葡萄糖基葡糖胺（7）及其α-d-呋喃糖类似物（1）和1- N， 3-O-羰基-α-d-呋喃呋喃糖胺（15）及其α-d-吡喃糖类似物（17）。类似地，α-d-吡喃吡喃糖基叠氮化物得到1-N，2-O-羰基-α-d-吡喃吡喃糖基胺（9）和其α-d-呋喃糖类似物（3），以及1-N，3-O-羰基-胺基。 α-d-核吡喃糖基胺（19）及其β-d-木吡喃糖类似物（21）。产物及其乙酰化衍生物的结构通过1 H和13 C NMR光谱确定。当水中1,2-（环状氨基甲酸酯）5自发重排为21时，从β-d-吡喃并吡喃糖基叠氮化物获得1-N，3-O-羰基-β-d-吡喃并吡喃糖基胺（21）。
• KOVACS, JOZSEF;PINTER, ISTVAN;LENDERING, URSULA;KOLL, PETER, CARBOHYDR. RES., 210,(1991) C. 155-166
  作者：KOVACS, JOZSEF、PINTER, ISTVAN、LENDERING, URSULA、KOLL, PETER

  DOI：——

  日期：——
• Zemplen et al., Chemische Berichte, 1936, vol. 69, p. 748,752
  作者：Zemplen et al.

  DOI：——

  日期：——
• New glyco-oxazolidin-2-ones as chiral auxiliaries in boron-mediated asymmetric aldol reactions
  作者：Michael Stöver、Arne Lützen、Peter Köll

  DOI：10.1016/s0957-4166(99)00503-0

  日期：2000.2

  Two new chiral glyco-oxazolidin-2-one auxiliaries based on D-glucose are described. Some N-acyl derivatives were synthesized and used in dialkylboron-mediated asymmetric aldol reactions. All reactions delivered as the major diastereomer those predicted by the Zimmerman-Traxler model and were separated by column chromatography and mostly isolated in moderate to good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.