Methyl 3-amino-2,3,6-trideoxy-2-fluoro-β-L-talopyranoside | 128854-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3-amino-2,3,6-trideoxy-2-fluoro-β-L-talopyranoside
• 英文别名: (2S,3S,4R,5R,6S)-4-amino-5-fluoro-6-methoxy-2-methyloxan-3-ol
• CAS: 128854-95-5
• 化学式: C₇H₁₄FNO₃
• 分子量: 179.191
• InChiKey: RXMPRRVDESQHGP-FHKSGDNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.71
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methyl 3-amino-2,3,6-trideoxy-2-fluoro-β-L-talopyranoside 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 10.25h， 生成 2,3,6-Trideoxy-2-fluoro-3-trifluoroacetamido-α-L-talopyranose
  参考文献：
  名称：

  Synthesis and biological activity of (R)-2′-fluorocarminomycin

  摘要：

  甲基3-氨基-2,3,6-三去氧-2-氟-(β-L-戊糖苷)被水解为自由糖，(R)-2-氟多诺霉素盐酸盐，后者被转化为α-1,4-二-O-乙酰-N-三氟乙酰衍生物。利用三甲基硅基三氟甲磺酸盐作为活化剂，后者与卡米诺霉素酮缩合，然后去保护基得到目标化合物。新型氟蒽环素衍生物对多种肿瘤细胞系的细胞毒性与母体卡米诺霉素相同，两种化合物对P-388小鼠白血病的活性相同，尽管氟衍生物的效力降低了4倍，似乎毒性也稍微降低了一些。关键词：(R)-2-氟多诺霉素盐酸盐，合成；(R)-2′-氟卡米诺霉素，合成和生物活性。

  DOI：

  10.1139/v90-314
• 作为产物：
  描述：

  methyl 3-azido-4-O-benzoyl-2,3,6-trideoxy-2-fluoro-α-D-ribo-hex-5-enopyranoside 在 palladium oxide on barium sulfate 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.17h， 生成 Methyl 3-amino-2,3,6-trideoxy-2-fluoro-β-L-talopyranoside
  参考文献：
  名称：

  Synthesis of 3-amino-2,3,6-trideoxy-2-fluoro-l-talose and -d-allose [(R)-2-fluoro-l-daunosamine and (R)-2-fluoro-d-ristosamine]

  摘要：

  The title compounds were synthesized (as methyl glycosides) starting from 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-beta-D-glucopyranose. Stereoselective methods of glycosylation gave, via the tri-O-acetylglycopyranosyl bromide, the methyl 2-deoxy-2-fluoro-alpha- and -beta-D-glucopyranoside triacetates. Each anomer was O-deacetylated and further transformed into the corresponding, 4,6-O-benzylidenated 3-triflate, and the triflates were converted by azide displacement into the 3-azido-2,3-dideoxy-2-fluoroglycosides having the D-allo configuration. Hanesssian-Hullar reaction then furnished the corresponding 6-bromo-6-deoxy-4-benzoates, which were dehydrobrominated to give the methyl 3-azido-4-O-benzoyl-2,3,6-tri-deoxy-2-fluoro-alpha- and -beta-D-ribo-hex-5-enopyranosides. Debenzoylation of the alpha-anomer, followed by catalytic hydrogenation, led to methyl 3-amino-2,3,6-trideoxy-2-fluoro-beta-L-talopyranoside [methyl (R)-2-fluoro-beta-L-daunosaminide], whereas the same sequence applied to the beta-anomer afforded methyl 3-amino-2,3,6-trideoxy-2-fluoro-beta-D-allopyranoside [methyl (R)-2-fluoro-beta-D-ristosaminide]. The overall yields for these 10-step sequences were 11-12 and 16%, respectively. The 1H- and 13C-n.m.r. data for the new fluoro sugar derivatives are discussed with respect to the dependence of JF,H and JF,C values on molecular geometry and substituent effects.

  DOI：

  10.1016/0008-6215(90)84168-t

文献信息

• BAER, HANS H.;HERNANDEZ, MATEO FERNANDO;SIEMSEN, LISA, CARBOHYDR. RES., 195,(1990) N, C. 225-245
  作者：BAER, HANS H.、HERNANDEZ, MATEO FERNANDO、SIEMSEN, LISA

  DOI：——

  日期：——
• BAER, HANS H.;MATEO, FERNANDO HERNANDEZ, CAN. J. CHEM., 68,(1990) N1, C. 2055-2059
  作者：BAER, HANS H.、MATEO, FERNANDO HERNANDEZ

  DOI：——

  日期：——