(+)-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pentane-1,3-diol | 472958-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pentane-1,3-diol
• 英文别名: (+)-(3R)-3-(2-Methoxy-3-methoxymethoxymethylpyridin-4-yl)-pentane-1,3-diol；(3R)-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pentane-1,3-diol
• CAS: 472958-59-1
• 化学式: C₁₄H₂₃NO₅
• 分子量: 285.34
• InChiKey: BTDCDZYHXGJKDD-CQSZACIVSA-N

物化性质

• 沸点：
  435.2±45.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  81
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pentane-1,3-diol 在 sodium chlorite 、 disodium hydrogenphosphate 、 2-甲基-2-丁烯 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 39.0h， 生成 (R)-3-Hydroxy-3-(2-methoxy-3-methoxymethoxymethyl-pyridin-4-yl)-pentanoic acid
  参考文献：
  名称：

  Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

  摘要：

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00632-4
• 作为产物：
  描述：

  2-甲氧基吡啶 在 四(三苯基膦)钯 、 4 A molecular sieve titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 L-(+)-酒石酸二乙酯 、 甲基锂 、 二异丙胺 、 N,N-二异丙基乙胺 、 copper(l) chloride 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 癸烷 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 46.5h， 生成 (+)-3-[2-methoxy-3-(methoxymethoxymethyl)pyridin-4-yl]pentane-1,3-diol
  参考文献：
  名称：

  Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans

  摘要：

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00632-4

文献信息

• Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins
  申请人：——

  公开号：US20030073840A1

  公开（公告）日：2003-04-17

  A method of synthesizing a compound having the formula: 1 from a compound having the formula: 2 wherein R 1 is hydrogen, fluorine, chlorine or SiR 5 R 6 R 7 , wherein R 5 , R 6 , and R 7 are independently the same or different an alkyl group or an aryl group, R 2 is an alkyl group, R 3 is a protecting group, R 4 is an alkyl group, an allyl group, a propargyl group —CO 2 H, or a benzyl group, R 8 is —CO 2 R 10 , wherein R 10 is an alkyl group or an aryl group, X 1 is OH and X 2 is H, includes the step of exposing compound (III) to at least one of an organic acid or an inorganic acid. A compound has the general formula (III).

  一种合成具有以下化学式的化合物的方法：1从具有以下化学式的化合物中进行：2其中R1为氢、氟、氯或SiR5R6R7，其中R5、R6和R7分别独立地为相同或不同的烷基基团或芳基基团，R2为烷基基团，R3为保护基团，R4为烷基基团、烯丙基团、丙炔基团、—CO2H或苄基团，R8为—CO2R10，其中R10为烷基基团或芳基基团，X1为OH，X2为H，包括将化合物(III)暴露于至少一种有机酸或无机酸中的步骤。化合物具有一般化学式(III)。
• US6723853B2
  申请人：——

  公开号：US6723853B2

  公开（公告）日：2004-04-20
• Asymmetric total synthesis of (20R)-homocamptothecin, substituted homocamptothecins and homosilatecans
  作者：Ana E Gabarda、Wu Du、Thomas Isarno、Raghuram S Tangirala、Dennis P Curran

  DOI：10.1016/s0040-4020(02)00632-4

  日期：2002.8

  An efficient asymmetric synthesis of a key DE lactone pyridone intermediate in the synthesis of homocamptothecin is reported. The synthesis is scalable and features a Stille coupling and a Sharpless asymmetric epoxidation as the key steps. The key intermediate has been parleyed into homocamptothecin and an assortment of fluorinated homocamptothecins and homosilatecans (7-silylhomocamptothecins), thereby providing the first asymmetric entry to this important new class of antitumor agents. (C) 2002 Published by Elsevier Science Ltd.