Methyl 3-[3-[bis(phenylmethoxy)methyl]-6-chloro-1,5,8-trimethoxynaphthalen-2-yl]-4-formyl-2-methoxy-6-methylbenzoate | 492453-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 3-[3-[bis(phenylmethoxy)methyl]-6-chloro-1,5,8-trimethoxynaphthalen-2-yl]-4-formyl-2-methoxy-6-methylbenzoate
• CAS: 492453-51-7
• 化学式: C₃₉H₃₇ClO₉
• 分子量: 685.17
• InChiKey: ZWPQKJFTYPJKBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Methyl 3-[3-[bis(phenylmethoxy)methyl]-6-chloro-1,5,8-trimethoxynaphthalen-2-yl]-4-formyl-2-methoxy-6-methylbenzoate 在 samarium diiodide 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以81%的产率得到methyl (5S,6S)-9-chloro-5-hydroxy-1,8,11,12-tetramethoxy-3-methyl-6-phenylmethoxy-5,6-dihydrobenzo[a]anthracene-2-carboxylate
  参考文献：
  名称：

  Semi-pinacol strategy for constructing B-ring of pradimicin–benanomicin antibiotics

  摘要：

  Semi-pinacol cyclization of compound 8, having an acetal and an aldehyde substituent, was achieved by employing SmI2 and BF3.OEt2, leading to the highly stereoselective formation of cyclized product 9. The vicinal diol in 9 is discriminated, so as to allow selective glycosylation for the synthesis of pradimicin-benanomicin antibiotics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01608-8
• 作为产物：
  描述：

  苄氧基三甲基硅烷 在 manganese(IV) oxide 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Methyl 3-[3-[bis(phenylmethoxy)methyl]-6-chloro-1,5,8-trimethoxynaphthalen-2-yl]-4-formyl-2-methoxy-6-methylbenzoate
  参考文献：
  名称：

  Semi-pinacol strategy for constructing B-ring of pradimicin–benanomicin antibiotics

  摘要：

  Semi-pinacol cyclization of compound 8, having an acetal and an aldehyde substituent, was achieved by employing SmI2 and BF3.OEt2, leading to the highly stereoselective formation of cyclized product 9. The vicinal diol in 9 is discriminated, so as to allow selective glycosylation for the synthesis of pradimicin-benanomicin antibiotics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01608-8

文献信息

• Semi-pinacol strategy for constructing B-ring of pradimicin–benanomicin antibiotics
  作者：Ken Ohmori、Mitsuru Kitamura、Yuji Ishikawa、Hirohisa Kato、Mami Oorui、Keisuke Suzuki

  DOI：10.1016/s0040-4039(02)01608-8

  日期：2002.9

  Semi-pinacol cyclization of compound 8, having an acetal and an aldehyde substituent, was achieved by employing SmI2 and BF3.OEt2, leading to the highly stereoselective formation of cyclized product 9. The vicinal diol in 9 is discriminated, so as to allow selective glycosylation for the synthesis of pradimicin-benanomicin antibiotics. (C) 2002 Elsevier Science Ltd. All rights reserved.