2-<(benzyloxycarbonyl)amino>-2-deoxy-D-mannopyranose | 3006-58-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<(benzyloxycarbonyl)amino>-2-deoxy-D-mannopyranose
• 英文别名: 2-benzyloxycarbonylamino-2-deoxy-D-mannose；2-N-carbobenzoxyl-2-deoxy-D-mannosamine；N-(carbobenzyloxy)-D-mannosamine；ManCbz；N-Carbobenzyloxy Mannosamine；benzyl N-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamate
• CAS: 3006-58-4；7474-40-0；13030-01-8；42890-10-8；42973-23-9；77059-32-6；121785-09-9
• 化学式: C₁₄H₁₉NO₇
• 分子量: 313.307
• InChiKey: FRTOTMQAWIIMKK-CEHFSTBQSA-N

物化性质

• 沸点：
  606.0±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-<(benzyloxycarbonyl)amino>-2-deoxy-D-mannopyranose 在 transaldolase 、 三氟乙酸 作用下， 反应 64.0h， 生成 5-N-carbobenzoxylamino-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester
  参考文献：
  名称：

  流感病毒对血凝的潜在抑制剂的合成：N-乙酰神经氨酸N-5类似物的化学酶制剂。

  摘要：

  描述了向神经氨酸2的化学酶途径。该方法基于由Neu5Ac醛缩酶催化的N-碳代苯甲氧基甘露糖胺（ManCBz）3到N-碳代苯并神经氨酸（Neu5CBz）4的转化。Neu5CBz 4转化为α-甲基糖苷8并脱保护得到游离胺2。此过程已按比例放大以生成10克数量的2。的N-酰化2产生几个新的N-酰基神经氨酸类似物; 在血凝抑制试验（HAI）中，已将它们评估为流感病毒与鸡红细胞粘附的抑制剂。神经氨酸2的这种制备 与其他文献程序进行比较。

  DOI：

  10.1016/s0040-4020(01)80502-0
• 作为产物：
  描述：

  D-mannosamine hydrochloride 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 反应 4.0h， 以65%的产率得到2-<(benzyloxycarbonyl)amino>-2-deoxy-D-mannopyranose
  参考文献：
  名称：

  流感病毒对血凝的潜在抑制剂的合成：N-乙酰神经氨酸N-5类似物的化学酶制剂。

  摘要：

  描述了向神经氨酸2的化学酶途径。该方法基于由Neu5Ac醛缩酶催化的N-碳代苯甲氧基甘露糖胺（ManCBz）3到N-碳代苯并神经氨酸（Neu5CBz）4的转化。Neu5CBz 4转化为α-甲基糖苷8并脱保护得到游离胺2。此过程已按比例放大以生成10克数量的2。的N-酰化2产生几个新的N-酰基神经氨酸类似物; 在血凝抑制试验（HAI）中，已将它们评估为流感病毒与鸡红细胞粘附的抑制剂。神经氨酸2的这种制备 与其他文献程序进行比较。

  DOI：

  10.1016/s0040-4020(01)80502-0

文献信息

• Chemoenzymatic synthesis of neuraminic acid analogs structurally varied at C-5 and C-9 as potential inhibitors of the sialidase from influenza virus
  作者：Makoto Murakami、Kiyoshi Ikeda、Kazuo Achiwa

  DOI：10.1016/0008-6215(95)00295-2

  日期：1996.1

  9-N-acyl-5-trifluoroacetyl methyl alpha-ketosides (1a-c) and their 2,3-didehydro analogs (2a-c) have been synthesized through Neu5Ac aldolase-catalyzed aldol reaction of 6-azido-2-benzyloxycarbonylamino-2-deoxy-D-mannose with sodium pyruvate. The six compounds were investigated as inhibitors of sialidase from influenza virus. Compound 2b, a 2,3-didehydro type, showed the most potent inhibitory activity

  通过Neu5Ac醛缩酶催化的6-叠氮基醛醇缩合反应合成了9-氨基或9-N-酰基-5-三氟乙酰基甲基α-酮苷（1a-c）及其2,3-didehydro类似物（2a-c）。 -2-丙酮氧基羰基氨基-2-脱氧-D-甘露糖。研究了这六种化合物作为流感病毒唾液酸酶的抑制剂。化合物2b（2，3-二氢氢化物类型）显示出对该酶最强的抑制活性（IC50> 7.8 microM），而化合物1a-c（如甲基α-糖苷）实际上没有活性（IC50> 100 microM） ）。
• A Chemoenzymatic Total Synthesis of the Neurogenic Starfish Ganglioside LLG‐3 Using an Engineered and Evolved Synthase
  作者：Jamie R. Rich、Stephen G. Withers

  DOI：10.1002/anie.201204578

  日期：2012.8.20

  An LLG‐3 oligosaccharide–fluoride (see scheme) can be assembled chemoenzymatically and readily coupled with various sphingosines by an engineered endoglycoceramidase glycosynthase. The lyso ganglioside products are acylated to generate the individual isomers identified in the heterogeneous natural isolates, as well as modified glycosphingolipids.

  LLG-3寡糖-氟化物（参见方案）可以通过化学酶组装，并可以通过工程改造的糖内酰胺酶糖合酶与各种鞘氨醇轻松偶联。所述溶血 神经节苷脂产物酰化，以产生在异构天然分离物识别的单独的异构体，以及修饰的鞘糖脂。
• Halogenation selective en c-6 de 2-amino-2-desoxy-d-glycopyranoses
  作者：Najat Belkhouya、Catherine Fre´chou、Mohammed Benazza、Daniel Beaupe`re、Raoul Uzan、Gilles Demailly

  DOI：10.1016/0040-4039(91)80604-5

  日期：1991.8

  N-protected 2-amino-2-deoxy-D-glycopyranoses can be selectively halogenated on C-6 by treatment with triphenylphosphine-carbone tetrahalide-pyridine.

  通过用三苯基膦-碳四卤化物-吡啶处理，可以在C-6上选择性地卤化N-保护的2-氨基-2-脱氧-D-Glycopyranoses。
• Versatile intermediates in the selective modification of the amino function of 2-amino-2-deoxy-d-mannopyranose and the 3-position of 2-acetamido-2-deoxy-d-mannose: Potential membrane modifiers in neoplastic control
  作者：Norman J. Angelino、Ralph J. Bernacki、Moheswar Sharma、Onda Dodson-Simmons、Walter Korytnyk

  DOI：10.1016/0008-6215(95)00154-l

  日期：1995.10

  A general method has been developed to selectively modify the amino group of 2-amino-2-deoxy-D-mannopyranose (D-mannosamine), a precursor of the terminal membrane sugar, sialic acid. 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate was prepared via two routes that allowed introduction of various acyl groups onto the amino function. These compounds were evaluated for their antineoplastic properties. The most significant preclinical therapeutic finding was the antileukemic activity found in mice for tetra-O-acetyl-2-epi-streptozotocin (the acetylated alpha-mannosamine epimer of streptozotocin). Administration of 50 mg/kg/day X 5 to leukemia L1210-bearing DBA/2Ha mice resulted in 5/5 35-day survivors. Neutralization of 1,3,3,6-tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate under aqueous conditions led to 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranose, the oxidation of which gave 2-acetamido-4,6-di-O-acetyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose. This agent demonstrated an IC50 of 25 mu M with a murine L1210 cell culture. Administration of 100 mg/kg/day X 5 resulted in 42% ILS in DBA/2 mice with ip L1210 leukemia. Several other nonacetylated derivatives were also prepared by direct N-acylation, producing, for example, fluorescently tagged N-dansylmannosamine.
• Facile chemoenzymic synthesis of 3-(hydroxymethyl)-6-epicastanospermine
  作者：Pengzu Zhou、Hamzah M. Salleh、John F. Honek

  DOI：10.1021/jo00053a051

  日期：1993.1