methyl (3S,5S)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate | 115408-07-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (3S,5S)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate
• 英文别名: methyl (3S,5S)-3,5,6-trihydroxy-5,6-O-isopropylidenehexanoate；methyl (3S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxybutanoate
• CAS: 115408-07-6
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: DWQVEBNRJGOPAY-YUMQZZPRSA-N

物化性质

• 沸点：
  315.6±22.0 °C(predicted)
• 密度：
  1.104±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3S,5S)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate 在 盐酸 、 sodium hydroxide 、 四丁基氟化铵 、 仲丁基锂 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 0.83h， 生成 4-[(2S,4R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,4-dihydroxy-pentyl]-N-((E)-propenyl)-nicotinamide
  参考文献：
  名称：

  Design and synthesis of bisubstrate analogues for 3-hydroxy-3-methyl-glutaryl coenzyme a reductase

  摘要：

  The coupling of metalated pyridine derivatives with a chiral Weinreb amide derived from gluconolactone followed by stereoselective reduction of the resulting ketone are the key steps of the synthesis of bisubstrates analogues of the HMGCoA reduction by HMGR.

  DOI：

  10.1016/0960-894x(96)00077-7
• 作为产物：
  描述：

  (S)-4-(2-羟乙基)-2,2-二甲基-1,3-二氧戊环 在 氢氧化钾 、 草酰氯 、 叔丁基氯化镁 、 二甲基亚砜 、 三乙胺 、 氢化铝 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 25.25h， 生成 methyl (3S,5S)-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate
  参考文献：
  名称：

  Bakers' yeast oxidation of methyl para-tolylsuifide: Synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents

  摘要：

  The use of (R)-methyl para-tolylsulfoxide as a chiral auxiliary in a novel synthesis of a key intermediate en route to mevinic acid-type hypocholestemic agents is described. The synthesis is short and simple consisting of eight steps to yield enantiomerically pure beta-silyloxy-delta-lactone. The chiral sulfoxide used in the synthesis was obtained via a straightforward biooxidation of methyl paratolylsulfide using bakers' yeast (Saccharomyces cerevisiae NCYC 73). The biotransformation involves the use of whole cells and affords the sulfoxide in good yield and with high stereoselectivity.

  DOI：

  10.1016/0040-4020(95)00819-t

文献信息

• AMIDE COMPOUNDS AND THEIR USE AS ANTITUMOR AGENTS
  申请人：Hanessian Stephan

  公开号：US20100113504A1

  公开（公告）日：2010-05-06

  The present invention relates to a compound of Formula (I), its geometrical isomers, in an optically active form as enantiomers, diastereomers, as well as in the form of racemate, as well as pharmaceutically acceptable salts thereof, wherein R is selected from CONHOH, CONHCH 2 SH, CONHCH 2 SCOCH 3 , SH, SCOCH 3 , SCH 3 , N(OH)COH, COCONHCH 3 and CF 3 for the preparation of a medicament, in particular for selectively inducing terminal differentiation of neoplastic cells and thereby inhibiting proliferation of such cells, for inducing differentiation of tumor cells in a tumor, for inhibiting the activity of histone deacetylase and for the treatment of primary cancer or secondary cancer.

  本发明涉及一种公式(I)的化合物，其几何异构体，以光学活性形式作为对映体，对映异构体，以及盐的形式，其中R选自CONHOH，CONHCH2SH，CONHCH2SCOCH3，SH，SCOCH3，SCH3，N（OH）COH，COCONHCH3和CF3，用于制备药物，特别是用于选择性诱导肿瘤细胞的终端分化，从而抑制这些细胞的增殖，诱导肿瘤中肿瘤细胞的分化，抑制组蛋白去乙酰化酶的活性以及治疗原发性癌症或转移性癌症。
• Mahler, Ulrike; Devant, Ralf M.; Braun, Manfred, Chemische Berichte, 1988, vol. 121, p. 2035 - 2044
  作者：Mahler, Ulrike、Devant, Ralf M.、Braun, Manfred

  DOI：——

  日期：——
• MAHLER, ULRIKE;DEVANT, RALF M.;BRAUN, MANFRED, CHEM. BER., 121,(1988) N 11, C. 2035-2044
  作者：MAHLER, ULRIKE、DEVANT, RALF M.、BRAUN, MANFRED

  DOI：——

  日期：——
• Bakers' yeast oxidation of methyl para-tolylsuifide: Synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents
  作者：Jenny Tang、Ian Brackenridge、Stanley M. Roberts、Jean Beecher、Andrew J. Willetts

  DOI：10.1016/0040-4020(95)00819-t

  日期：1995.11

  The use of (R)-methyl para-tolylsulfoxide as a chiral auxiliary in a novel synthesis of a key intermediate en route to mevinic acid-type hypocholestemic agents is described. The synthesis is short and simple consisting of eight steps to yield enantiomerically pure beta-silyloxy-delta-lactone. The chiral sulfoxide used in the synthesis was obtained via a straightforward biooxidation of methyl paratolylsulfide using bakers' yeast (Saccharomyces cerevisiae NCYC 73). The biotransformation involves the use of whole cells and affords the sulfoxide in good yield and with high stereoselectivity.
• Design and synthesis of bisubstrate analogues for 3-hydroxy-3-methyl-glutaryl coenzyme a reductase
  作者：C Taillefumier、D de Fornel、Y Chapleur

  DOI：10.1016/0960-894x(96)00077-7

  日期：1996.3

  The coupling of metalated pyridine derivatives with a chiral Weinreb amide derived from gluconolactone followed by stereoselective reduction of the resulting ketone are the key steps of the synthesis of bisubstrates analogues of the HMGCoA reduction by HMGR.