methyl (2R)-2-(benzhydrylideneamino)-3-[tert-butyl(dimethyl)silyl]oxypropanoate | 208253-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2R)-2-(benzhydrylideneamino)-3-[tert-butyl(dimethyl)silyl]oxypropanoate
• CAS: 208253-69-4
• 化学式: C₂₃H₃₁NO₃Si
• 分子量: 397.59
• InChiKey: KQLJTUWBOXHEMO-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-(benzhydrylideneamino)-3-[tert-butyl(dimethyl)silyl]oxypropanoate 在 吡啶 、 4-二甲氨基吡啶 、 锂硼氢 、 K₂Os(OH)4 、 TRIBAl 、 二异丁基氢化铝 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 70.0h， 生成 (2R,3S,4R)-N-diphenylmethyl-5-O-tert-butyldimethylsilyl-4-aminopentane-1,2,3,5-tetraol
  参考文献：
  名称：

  （-）-8-表-swainsonine三乙酸酯和（+）-1，2-Di-表-swainsonine的不对称合成。羰基加成因空前的氮杂频哪醇重排而受阻。

  摘要：

  从衍生自D-丝氨酸的O'Donnell Schiff碱酯1合成吲哚并核苷（-）-8-表-swainsonine三乙酸酯和（+）-1，2-二-表-swainsonine。（i）（）Bu（5）Al（2）H / H（2）C = CHMgBr的1的还原烯基化，然后用OsO（4）对悬挂的烯丙基进行底物定向二羟基化，还原亚胺，和与Ph（3）P / CCl（4）环合得到多羟基吡咯烷8a和8b作为高级中间体。有效的保护基操作将吡咯烷8a和8b转化为其相应的部分受保护的类似物10a和10b，它们经Swern氧化和与BF（3）的非对映选择性Keck型烯丙基化.Et（2）O提供了所需的三碳同系物（10a， > 20：1 de; 10b，3.5：1 de）。使用螯合的路易斯酸MgBr（2）代替BF（3）。带有10a的Et（2）O导致aza碳上的新型氮杂频哪醇重排和烯丙基化，生成氨基醇17，这类似于吲哚izidin

  DOI：

  10.1021/jo000527u
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (R)-2-(Benzhydrylidene-amino)-3-hydroxy-propionic acid methyl ester 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以86%的产率得到methyl (2R)-2-(benzhydrylideneamino)-3-[tert-butyl(dimethyl)silyl]oxypropanoate
  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

• Lipo α-Amino-β-hydroxy Acids and O-Linked Glycosides:  Building Blocks for Ceramyl and Glycosphingoyl Peptides
  作者：Michael M. Palian、Robin Polt

  DOI：10.1021/jo015844v

  日期：2001.10.1
• New PDMP analogues inhibit process outgrowth in an insect cell line
  作者：Jacob P. Slavish、Donna K. Friel、Lynne A. Oland、Robin Polt

  DOI：10.1016/j.bmcl.2004.01.013

  日期：2004.3

  D-threo-1-Phenyl-2-aminodecanoyl-3-morpholinopropanol (D-threo-PDMP) has previously been shown to inhibit the biosynthesis of glycosphingolipids (GSLs) in mammals and mammalian cell lines by the inhibition of glucosylceramide synthase. New D-threo-PDMP analogues were synthesized from D-serine, and found to suppress neurite extension in an embryonic insect cell line from the moth Manduca sexta, and in explanted neural tissue from insect pupae. Inhibition occurred at lower concentrations than D-threo-PDMP. The observed suppression of neurite formation was found to be reversible after the removal of the compounds. Due to their small size and short life cycle, M. sexta is shown to be an ideal model organism for studies of GSL effects in cellular development, and for drug development studies. (C) 2004 Elsevier Ltd. All rights reserved.
• Syntheses of iminolyxitols via tandem reduction-alkenylation of O'Donnell's Schiff bases
  作者：Hossein Razavi、Robin Polt

  DOI：10.1016/s0040-4039(98)00495-x

  日期：1998.5

  The concise enantioselective synthesis of iminolyxitol glycosidase inhibitors starting from bentophenone imines of D-serine and L-alanine esters is very efficient. The reductive-alkenylation of the Schiff bases followed by substrate-directed dihydroxylation and amino dehydration gave the polyhydroxylated pyrrolidines in excellent overall yields (19.6% for (3) under bar --> (8) under bar, 9.9% for (9) under bar --> <(13)under bar>.) (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.
• Asymmetric Syntheses of (−)-8-<i>e</i><i>pi</i>-Swainsonine Triacetate and (+)-1,2-Di-<i>e</i><i>pi</i>-swainsonine. Carbonyl Addition Thwarted by an Unprecedented Aza-Pinacol Rearrangement
  作者：Hossein Razavi、Robin Polt

  DOI：10.1021/jo000527u

  日期：2000.9.1

  pyrrolidines 8a and 8b as advanced intermediates. Efficient protecting group manipulations converted pyrrolidines 8a and 8b to their corresponding partially protected analogues 10a and 10b, which upon Swern oxidation and diastereoselective Keck-type allylation with BF(3).Et(2)O afforded the required three-carbon homologues (10a, >20:1 de; 10b, 3.5:1 de). Use of the chelating Lewis acid MgBr(2) instead of BF(3)

  从衍生自D-丝氨酸的O'Donnell Schiff碱酯1合成吲哚并核苷（-）-8-表-swainsonine三乙酸酯和（+）-1，2-二-表-swainsonine。（i）（）Bu（5）Al（2）H / H（2）C = CHMgBr的1的还原烯基化，然后用OsO（4）对悬挂的烯丙基进行底物定向二羟基化，还原亚胺，和与Ph（3）P / CCl（4）环合得到多羟基吡咯烷8a和8b作为高级中间体。有效的保护基操作将吡咯烷8a和8b转化为其相应的部分受保护的类似物10a和10b，它们经Swern氧化和与BF（3）的非对映选择性Keck型烯丙基化.Et（2）O提供了所需的三碳同系物（10a， > 20：1 de; 10b，3.5：1 de）。使用螯合的路易斯酸MgBr（2）代替BF（3）。带有10a的Et（2）O导致aza碳上的新型氮杂频哪醇重排和烯丙基化，生成氨基醇17，这类似于吲哚izidin