(3β,5β,12α)-3-[[(4S)-4-amino-5-methoxy-1,5-dioxopentyl]amino]-12-hydroxycholan-24-oic acid methyl ester | 280765-93-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3β,5β,12α)-3-[[(4S)-4-amino-5-methoxy-1,5-dioxopentyl]amino]-12-hydroxycholan-24-oic acid methyl ester
• 英文别名: (3β,5β,12α)-3-[[4(S)-4-amino-5-methoxy-1,5-dioxopentyl]amino]-12-hydroxycholan-24-oic acid methyl ester；[3β(S),5β,12α]-3-[[4-amino-5-methoxy-1,5-dioxopentyl]amino]-12-hydroxycholan-24-oic acid methyl ester；methyl (2S)-2-amino-5-[[(3S,5R,8R,9S,10S,12S,13R,14S,17R)-12-hydroxy-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]-5-oxopentanoate
• CAS: 280765-93-7
• 化学式: C₃₁H₅₂N₂O₆
• 分子量: 548.764
• InChiKey: ITEJYRXOEZMHOT-IAQBOCIOSA-N

物化性质

• 熔点：
  121 °C
• 沸点：
  672.7±55.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3β,5β,12α)-3-[[(4S)-4-amino-5-methoxy-1,5-dioxopentyl]amino]-12-hydroxycholan-24-oic acid methyl ester 在 N,N-二异丙基乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 178.0h， 生成 [3β(S),5β,12α]-3-[[4-[[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl][2-(1,1-dimethylethoxy)-2-oxoethyl]amino]-5-methoxy-1,5-dioxopentyl]amino]-12-hydroxycholan-24-oic acid methyl ester
  参考文献：
  名称：

  Blood pool agents for nuclear magnetic resonance diagnostics

  摘要：

  公开号：

  EP1935435B1
• 作为产物：
  描述：

  1-benzyl 2-methyl (S)-5-oxopyrrolidine-1,2-dicarboxylate 在 5%-palladium/activated carbon 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 56.5h， 生成 (3β,5β,12α)-3-[[(4S)-4-amino-5-methoxy-1,5-dioxopentyl]amino]-12-hydroxycholan-24-oic acid methyl ester
  参考文献：
  名称：

  Blood pool agents for nuclear magnetic resonance diagnostics

  摘要：

  公开号：

  EP1935435B1

文献信息

• A process for the preparation of 3-Glutamido bile ester derivatives using N-tBoc methyl pyroglutamate
  申请人：Bracco Imaging S.p.A.

  公开号：EP1229041A1

  公开（公告）日：2002-08-07

  The present invention relates to a novel process for the preparation of bile esters derivatives of general formula (I), in which R1 is H or OH; R2 is H, α-OH or β-OH and R3 is a straight or branched C1-C4 alkyl group or a benzyl group. The process uses either L-glutamic acid hydrochloride (II) or L-glutamic acid as starting material, according to the following Scheme 1.

  本发明涉及一种新型的制备一般式（I）中胆汁酯衍生物的过程，其中R1为H或OH；R2为H，α-OH或β-OH，R3为直链或支链C1-C4烷基或苯甲基。该过程使用L-谷氨酸盐酸盐（II）或L-谷氨酸作为起始材料，根据以下方案1进行。
• Scale-Up of Trisodium [(3β,5β,12α)-3-[[4(<i>S</i>)-4-[Bis[2-[bis[(carboxy-<i>kO</i>)methyl]amino-<i>kN</i>]ethyl]amino-<i>kN</i>]-4-(carboxy-<i>kO</i>)-1-oxobutyl]amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)], a Gd(III) Complex under Development As a Contrast Agent for MRI Coronary Angiography
  作者：Pier Lucio Anelli、Marino Brocchetta、Luciano Lattuada、Giuseppe Manfredi、Pierfrancesco Morosini、Marcella Murru、Daniela Palano、Marco Sipioni、Massimo Visigalli

  DOI：10.1021/op900008a

  日期：2009.7.17

  Process chemistry involved in the discovery and development routes to trisodium [(3 beta,5 beta,12(alpha)-3-[[4(S)-4-[bis[2-[bis[(carboxy-kO)methyl]amino-kN]ethyl]amino-kN]4-(carboxy-kO)-1-oxobutyl]- amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)] (B22956/1) starting from L-glutamic acid and (3 alpha,5 beta,12 alpha)-3,12-dihydroxycholan-24-oic acid is described. The best process is based on seven chemical steps and overcomes difficult purification protocols. Such process has been successfully implemented to prepare multikilogram batches of the target compound in 20% overall yield from (3 alpha,5 beta,12 alpha)-3,12-dihydroxycholan-24-oic acid.