(1S,2S)-1-phenyl-amino-3-O-tertbutyldimethylsilyloxy-1-propanol | 131472-79-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,2S)-1-phenyl-amino-3-O-tertbutyldimethylsilyloxy-1-propanol
• 英文别名: 2-(S)-amino-3-(tert-butyldimethylsilanyloxy)-1-(S)-phenylpropan-1-ol；(1S,2S)-2-amino-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-1-ol
• CAS: 131472-79-2
• 化学式: C₁₅H₂₇NO₂Si
• 分子量: 281.47
• InChiKey: RCEXJSANYAGMCX-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1-phenyl-amino-3-O-tertbutyldimethylsilyloxy-1-propanol 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 氢氟酸 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 64.0h， 生成 L-threo-2-amino-3-morpholino-1-phenylpropan-1-ol
  参考文献：
  名称：

  Glycosyltransferase Inhibitors:  Synthesis of d-threo-PDMP, l-threo-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from d- or l-Serine

  摘要：

  The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2-decanoylamino-3-N-morpholino-1- propanol (L-threo-PDMP) (la) from L-serine, and the enantiomer (1R,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (Ib) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the beta-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure Ib in high yield after six steps. Three other D-threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D-threo-PDPP (le). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.

  DOI：

  10.1021/jo980951j
• 作为产物：
  描述：

  (1S,2S)-2-[N-(diphenylmethylene)amino]-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol 在 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到(1S,2S)-1-phenyl-amino-3-O-tertbutyldimethylsilyloxy-1-propanol
  参考文献：
  名称：

  Glycosyltransferase Inhibitors:  Synthesis of d-threo-PDMP, l-threo-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from d- or l-Serine

  摘要：

  The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2-decanoylamino-3-N-morpholino-1- propanol (L-threo-PDMP) (la) from L-serine, and the enantiomer (1R,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (Ib) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the beta-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure Ib in high yield after six steps. Three other D-threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D-threo-PDPP (le). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.

  DOI：

  10.1021/jo980951j

文献信息

• Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase
  申请人：Bradley Stuart Edward

  公开号：US20090023703A1

  公开（公告）日：2009-01-22

  Compounds represented by Formula (I): or pharmaceutically acceptable salts thereof, are inhibitors of glycogen phosphorylase and are useful in the prophylactic or therapeutic treatment of diabetes, hyperglycemia, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis or tissue ischemia e.g. myocardial ischemia, and as cardioprotectants.

  由式（I）表示的化合物或其药学上可接受的盐，是糖原磷酸化酶的抑制剂，可用于预防或治疗糖尿病、高血糖、高胆固醇血症、高胰岛素血症、高脂血症、高血压、动脉硬化或组织缺血（例如心肌缺血），以及作为心脏保护剂。
• [EN] PYRROLOPYRIDINE-2-CARBOXYLIC ACID AMIDE INHIBITORS OF GLYCOGEN PHOSHORYLASE<br/>[FR] INHIBITEURS D'AMIDE D'ACIDE PYRROLOPYRIDINE-2-CARBOXYLIQUE DE LA GLYCOGENE PHOSPHORYLASE
  申请人：OSI PHARM INC

  公开号：WO2004104001A3

  公开（公告）日：2005-03-03
• 2-Amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones
  作者：Tamas E Gunda、Ferenc Sztaricskai

  DOI：10.1016/s0040-4020(97)00483-3

  日期：1997.6

  3,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3 -phthalimido-4-styrylazetidinones were obtained in optically pure form by chiral Staudinger reaction. The cis-alpha/beta-ratio could be influenced by: the protective groups of the diol moiety. Removal of the chiral auxiliarity could be accomplished by direct oxidation, or by previous double bond formation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary. (C) 1997 Elsevier Science Ltd.
• POLT, ROBIN;PETERSON, MATT A., TETRAHEDRON LETT., 31,(1990) N5, C. 1985-1986
  作者：POLT, ROBIN、PETERSON, MATT A.

  DOI：——

  日期：——
• Glycosyltransferase Inhibitors:  Synthesis of <scp>d</scp>-<i>threo</i>-PDMP, <scp>l</scp>-<i>threo</i>-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from <scp>d</scp>- or <scp>l</scp>-Serine
  作者：Scott A. Mitchell、Bryan D. Oates、Hossein Razavi、Robin Polt

  DOI：10.1021/jo980951j

  日期：1998.11.1

  The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2-decanoylamino-3-N-morpholino-1- propanol (L-threo-PDMP) (la) from L-serine, and the enantiomer (1R,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (Ib) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the beta-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure Ib in high yield after six steps. Three other D-threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D-threo-PDPP (le). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.