(3β,5β,12α)-12-hydroxy-[[2-(hydroxymethyl)benzoyl]amino]cholan-24-oic acid methyl ester | 328068-12-8

• 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)-12-hydroxy-[[2-(hydroxymethyl)benzoyl]amino]cholan-24-oic acid methyl ester
• 英文别名: methyl (4R)-4-[(3S,5R,8R,9S,10S,12S,13R,14S,17R)-12-hydroxy-3-[[2-(hydroxymethyl)benzoyl]amino]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 328068-12-8
• 化学式: C₃₃H₄₉NO₅
• 分子量: 539.756
• InChiKey: JPUXYWHRPCJVDX-ZTQDQIAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3β,5β,12α)-12-hydroxy-[[2-(hydroxymethyl)benzoyl]amino]cholan-24-oic acid methyl ester 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以85%的产率得到(3β,5β,12α)-3-amino-12-hydroxycholan-24-oic acid methyl ester
  参考文献：
  名称：

  Scale-Up of Trisodium [(3β,5β,12α)-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-)], a Gd(III) Complex under Development As a Contrast Agent for MRI Coronary Angiography

  摘要：

  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.

  DOI：

  10.1021/op900008a
• 作为产物：
  描述：

  (3β,5β,12α)-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-12-hydroxycholan-24-oic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.0h， 以99%的产率得到(3β,5β,12α)-12-hydroxy-[[2-(hydroxymethyl)benzoyl]amino]cholan-24-oic acid methyl ester
  参考文献：
  名称：

  Scale-Up of Trisodium [(3β,5β,12α)-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-)], a Gd(III) Complex under Development As a Contrast Agent for MRI Coronary Angiography

  摘要：

  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.

  DOI：

  10.1021/op900008a

文献信息

• Bile acid salts
  申请人：BRACCO INTERNATIONAL B.V.

  公开号：US20020019549A1

  公开（公告）日：2002-02-14

  A process for the preparation of the compounds of general formula (I) 1 in which R 1 is H or OH; R 2 is H, &agr;-OH, or &bgr;-OH; and R 3 is a straight or branched C 1 -C 4 alkyl group or a benzyl group, comprising the reduction of compounds of formula (III) 2 wherein R 1 , R 2 and R 3 have the same meanings as in formula I, in the presence of sodium borohydride.

  通式(I)化合物的制备工艺 1 其中 R 1 是 H 或 OH； R 2 是 H、&agr;-OH 或 &bgr;-OH；和 R 3 是直链或支链 C 1 -C 4 烷基或苄基、 包括式（III）化合物的还原反应 2 其中 R 1 , R 2 和 R 3 在硼氢化钠存在下，与式 I 中的含义相同。
• A PROCESS FOR THE PREPARATION OF 3-AMINO BILE ACID DERIVATIVES
  申请人：BRACCO IMAGING S.p.A.

  公开号：EP1210359B1

  公开（公告）日：2005-05-11
• US6479681B2
  申请人：——

  公开号：US6479681B2

  公开（公告）日：2002-11-12