2-acetamido-1,2-dideoxy-1-nitro-D-mannitol | 14199-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-1,2-dideoxy-1-nitro-D-mannitol
• 英文别名: 2-acetylamino-1-nitro-1,2-dideoxy-D-mannitol；2-Acetylamino-1-nitro-1,2-didesoxy-D-mannit；2-(Acetyl-amino)-1,2-didesoxy-1-nitro-mannit；1-Nitro-2-acetamido-1,2-dideoxy-D-mannitol；2-(Acetylamino)-1,2-dideoxy-1-nitro-D-mannitol；N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-nitrohexan-2-yl]acetamide
• CAS: 14199-86-1
• 化学式: C₈H₁₆N₂O₇
• 分子量: 252.224
• InChiKey: GTLVBKOTJMCFBC-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  156
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-acetamido-1,2-dideoxy-1-nitro-D-mannitol 在 异氰酸苯酯 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 44.7h， 生成 3-[(R)-Acetylamino-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-5-hydroxy-4,5-dihydro-isoxazole-5-carboxylic acid
  参考文献：
  名称：

  Kettenverlängerung von 1-desoxy-1-nitroalditolen durch nitriloxid-cycloaddition. Synthese von 4-N-substituierten 3,4-didesoxy-2-ulosonsäuren

  摘要：

  Treatment of protected nitroalditols 1a or 2 with silylenolpyruvate (3) or methyl acrylate leads via nitrile oxide cycloadditon to cycle-tautomers of oximes, 5 or 4, respectively 4,5-dihydro-isoxazole 6. N-Acetyl-4-deoxy-4-(E/Z)-hydroxyimino-neuraminic acid (7) is obtained by deprotection of 4. Hydrogenation of 7 yields N-acetyl-4-amino-4-deoxy-neuraminic acid (9) and pentahydroxy-nononic acids 12a,b. The synthesis is useful for the chain extension of protected nitroalditols 13a and 20a, to give the corresponding oximes 15 and 22. This work provides a general method for the extension of sugar chains by three C-atoms and thus a novel synthesis of cr-keto acids containing an oxime and amino function. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00168-9
• 作为产物：
  描述：

  阿拉伯糖 在 硫酸 、 氨 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 35.0h， 生成 2-acetamido-1,2-dideoxy-1-nitro-D-mannitol
  参考文献：
  名称：

  4-脱氧-4-硝基唾液酸的合成。

  摘要：

  从开始的七个步骤中完成了4-deoxy-4-nitrosialic acid（3,4,5-trideoxy-4-nitro-D-glycero-beta-D-galacto-non-2-ulyryranosonic acid，5）的合成。来自D-阿拉伯糖。6碳片段2-乙酰氨基-1,2-二脱氧-1-硝基-D-甘露醇（6）与α-（溴甲基）丙烯酸乙酯的偶联得到5-乙酰氨基-2的2：1混合物， 3,4,5-四脱氧-2-亚甲基-4-硝基-D-甘油-D-半乳糖壬酸酯（9a-S）和乙基5-乙酰氨基-2,3,4,5-四脱氧-2-亚甲基- 4-硝基-D-甘油-D-talo-壬酸酯（9a-R）。对该烯酮的混合物进行臭氧分解，并在还原该臭氧化物后，将所得产物环化成吡喃糖苷。通过分步结晶分离目标化合物4-脱氧-4-硝基唾液酸乙酯（11a）。乙酯的水解被证明是有问题的。因此，通过使用α-（溴甲基）丙烯酸叔丁酯对合成

  DOI：

  10.1039/b605218e

文献信息

• AN ASYMMETRIC SYNTHESIS OF<scp>D</scp>- AND<scp>L</scp>-MANNOSAMINE
  作者：A. N. O'Neill

  DOI：10.1139/v59-253

  日期：1959.10.1

  The addition of ammonia to the ethylenic bond of D-arabo-tetraacetoxy-1-nitrohexene-1 was stereospecific and formed a crystalline product, 1-nitro-1-deoxy-N-acetyl-D-mannosaminol. Application of the Nef reaction to this compound gave 2-amino-2-deoxy-D-mannose, which was isolated as the crystalline pentaacetate and further characterized as the hydrochloride by deacetylation with hydrochloric acid. In the deacetylation of the pentaacetate with barium methoxide, however, an abnormal epimerization occurred to yield N-acetyl-D-glucosamine.L-Mannosamine pentaacetate was synthesized in a similar manner from L-arabo-tetra-acetoxy-1-nitrohexene-1.

  对D-arabo-tetraacetoxy-1-nitrohexene-1的乙烯基键加入氨是立体特异性的，并形成了结晶产物1-硝基-1-去氧-N-乙酰-D-甘露氨基醇。将Nef反应应用于这种化合物，得到2-氨基-2-去氧-D-甘露糖，它以结晶五乙酰基盐的形式被分离，并通过用盐酸脱乙酰化来进一步表征为盐酸盐。然而，在用钡甲氧化物脱乙酰化五乙酰基盐时，发生了异常的外消旋反应，产生了N-乙酰-D-葡萄糖胺。类似地，L-arabo-tetra-acetoxy-1-nitrohexene-1也可以合成L-甘露氨基醇五乙酰基盐。
• Concerning the Synthesis of D-Mannosamine and D-Glucosamine from D-arabo-3,4,5,6-Tetraacetoxy-1-nitro-1-hexene
  作者：John C. Sowden、Marvin L. Oftedahl

  DOI：10.1021/ja01494a050

  日期：1960.5
• Sowden; Oftedahl in R.L.Whistler; M.L.Wolfrom, Methods in Carbohydrate Chemistry, Bd.1 <New York 1962>S.235
  作者：Sowden、Oftedahl in R.L.Whistler、M.L.Wolfrom

  DOI：——

  日期：——
• Sowden; Oftedahl, R.L.Whistler,M.L.Wolfrom,Methods in Carbohydrate Chemistry,Bd.1<New York 1962>S.235
  作者：Sowden、Oftedahl

  DOI：——

  日期：——
• Kettenverlängerung von 1-desoxy-1-nitroalditolen durch nitriloxid-cycloaddition. Synthese von 4-N-substituierten 3,4-didesoxy-2-ulosonsäuren
  作者：Hans Mack、Reinhard Brossmer

  DOI：10.1016/s0040-4020(98)00168-9

  日期：1998.4

  Treatment of protected nitroalditols 1a or 2 with silylenolpyruvate (3) or methyl acrylate leads via nitrile oxide cycloadditon to cycle-tautomers of oximes, 5 or 4, respectively 4,5-dihydro-isoxazole 6. N-Acetyl-4-deoxy-4-(E/Z)-hydroxyimino-neuraminic acid (7) is obtained by deprotection of 4. Hydrogenation of 7 yields N-acetyl-4-amino-4-deoxy-neuraminic acid (9) and pentahydroxy-nononic acids 12a,b. The synthesis is useful for the chain extension of protected nitroalditols 13a and 20a, to give the corresponding oximes 15 and 22. This work provides a general method for the extension of sugar chains by three C-atoms and thus a novel synthesis of cr-keto acids containing an oxime and amino function. (C) 1998 Elsevier Science Ltd. All rights reserved.