2-acetamido-4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enono-1,5-lactone | 34051-46-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetamido-4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enono-1,5-lactone
• 英文别名: 2-acetamido-4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-1,5-lactone；[(2R,3S)-5-acetamido-3-acetyloxy-6-oxo-2,3-dihydropyran-2-yl]methyl acetate
• CAS: 34051-46-2
• 化学式: C₁₂H₁₅NO₇
• 分子量: 285.254
• InChiKey: DIPDELRICSHNQY-WDEREUQCSA-N

物化性质

• 沸点：
  397.1±35.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-acetamido-4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enono-1,5-lactone 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到3-(Acetamido)-6-(acetoxymethyl)-2H-pyran-2-one
  参考文献：
  名称：

  Ready Conversion of Sugar Derived 5,6-Dihydro-2-pyrones into 3-Acyloxy- and 3-Acylamido-2-Pyrones

  摘要：

  5-酰氧基-6-酰氧甲基-5,6-二氢-2-吡喃酮衍生物（1a, b和3b）及5-酰氧基-6-甲基-5,6-二氢-2-吡喃酮（3a），通过对2-氨基-2-脱氧-D-葡糖酸或L-鼠李糖和D-葡糖-1,5-内酯的酰基化反应，和锡（IV）氯化物反应，生成3-酰胺基和3-酰氧基-6-酰氧甲基-2-吡喃酮（2a, b和4b，分别）以及3-苯甲氧基-6-甲基-2-吡喃酮（4a），产率极高。在延长反应时间（5小时）后，吡喃酮4b发生了通过氯取代烯丙基苯甲酸酯的反应，得到相应的6-氯甲基衍生物4c。

  DOI：

  10.1055/s-1991-26383
• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-manno-1,5-lactone 在 水 、 potassium carbonate 作用下， 以 乙酸乙酯 为溶剂， 以25%的产率得到2-acetamido-4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enono-1,5-lactone
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/0008-6215(95)00154-l

文献信息

• Confirmation of the structures of the products obtained on acylation of 2-amino-2-deoxy-d-gluconic acid
  作者：Derek Horton、James K. Thomson、Oscar Varela、Alejandro Nin、Rosa M. de Lederkremer

  DOI：10.1016/0008-6215(89)85106-7

  日期：1989.10

  Acetylation of 2-amino-2-deoxy-D-gluconic acid (1) with acetyl chloride-pyridine gave 2,3-unsaturated six- and five-membered lactones (2 and 3). Their benzoylated analogs (4 and 5) were obtained by benzoylation of 1 with benzoyl chloride-pyridine. Reaction of 1 with hot acetic anhydride-sodium acetate gave a approximately 1:2 mixture of (E)- and (Z)-2-acetamido-6-acetoxyhexa-2,4-dien-4-olide (6-E and

  2-氨基-2-脱氧-D-葡萄糖酸（1）与乙酰氯-吡啶的乙酰化得到2，3-不饱和的六元和五元内酯（2和3）。它们的苯甲酰化类似物（4和5）是通过用苯甲酰氯-吡啶对1进行苯甲酰化而获得的。1与热乙酸酐-乙酸钠反应制得（E）-和（Z）-2-乙酰氨基-6-乙酰氧基己基2,4-二烯-4-乙内酰胺（6-E和6）的约1：2混合物-Z）。用1，8-二氮杂双环[5.4.0]十一烷基-7-烯处理3也得到主要产物6-Z，其是从反应混合物中分离出的结晶。应用于化合物5的相同反应选择性地得到苯甲酰化的呋喃酮7的Z-异构体。混合物6-E，Z的部分和全部氢化（H2-Pd-C）分别得到外消旋的单不饱和内酯（8）和​​。双脱氧内酯（9），为此，确定了C-2和C-4的手性中心的苏式构型。从9酸除去乙酰基得到2-氨基-6-羟基-1,4-内酯盐酸盐10。另一方面，1（11）的4,6-O-亚苄基衍生物在高温下乙酰化。得到2，3-不
• HORTON, DEREK;THOMSON, JAMES K.;VARELA, OSCAR;NIN, ALEJANDRO;LEDERKREMER,+, CARBOHYDR. RES., 193,(1989) C. 49-60
  作者：HORTON, DEREK、THOMSON, JAMES K.、VARELA, OSCAR、NIN, ALEJANDRO、LEDERKREMER,+

  DOI：——

  日期：——