methyl 6-formyl-2-benzyloxycarbonylamino-4,5-dehydro-2,3,4-trideoxy-α-D-glucopyranoside | 1350556-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 6-formyl-2-benzyloxycarbonylamino-4,5-dehydro-2,3,4-trideoxy-α-D-glucopyranoside
• 英文别名: benzyl N-[(2S,3R)-6-formyl-2-methoxy-3,4-dihydro-2H-pyran-3-yl]carbamate
• CAS: 1350556-16-9
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: OVUUXZSENCBUNR-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-formyl-2-benzyloxycarbonylamino-4,5-dehydro-2,3,4-trideoxy-α-D-glucopyranoside 在 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以89%的产率得到methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,3,4-trideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Hybrid Aminoglycoside Antibiotics via Tsuji Palladium-Catalyzed Allylic Deoxygenation

  摘要：

  Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an alpha,beta-unsaturated 6'-aldehyde and an allylic 3'-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd-2(dba)(3) and Bu3P granted access to a novel series of 3',4'-dideoxy-4',5'-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

  DOI：

  10.1021/ol2027703
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 4-二甲氨基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 甲酸 、 三丁基膦 、 四丁基氟化铵 、 三氧化硫吡啶 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 106.25h， 生成 methyl 6-formyl-2-benzyloxycarbonylamino-4,5-dehydro-2,3,4-trideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Hybrid Aminoglycoside Antibiotics via Tsuji Palladium-Catalyzed Allylic Deoxygenation

  摘要：

  Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an alpha,beta-unsaturated 6'-aldehyde and an allylic 3'-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd-2(dba)(3) and Bu3P granted access to a novel series of 3',4'-dideoxy-4',5'-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

  DOI：

  10.1021/ol2027703

文献信息

• Hybrid Aminoglycoside Antibiotics <i>via</i> Tsuji Palladium-Catalyzed Allylic Deoxygenation
  作者：Stephen Hanessian、Juan Pablo Maianti、Rowena D. Matias、Lee Ann Feeney、Eliana S. Armstrong

  DOI：10.1021/ol2027703

  日期：2011.12.16

  Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an alpha,beta-unsaturated 6'-aldehyde and an allylic 3'-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd-2(dba)(3) and Bu3P granted access to a novel series of 3',4'-dideoxy-4',5'-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.