(R)-tert-butyl 4-((R)-1'-hydroxyprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate | 160592-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-tert-butyl 4-((R)-1'-hydroxyprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: (4R)-4-((1R)-1-hydroxy-prop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester；tert-butyl (4R)-4-[(1R)-1-hydroxyprop-2-ynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 160592-94-9
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: ZQKGOBZDKLCXMB-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 4-((R)-1'-hydroxyprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate 在 Lindlar's catalyst 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以96%的产率得到(4R,1'R)-4-(1-hydroxy-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A short route to N-protected furanomycin, 5′-epi-furanomycin and isofuranomycin derivatives

  摘要：

  A short new route to N-protected L-(+)-furanomycin and two of its isomeric derivatives has been developed, which featured the utility of D-serine as a chiral pool material and ring-closing metathesis as a key ring-forming step. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.032
• 作为产物：
  描述：

  (R)-tert-butyl 4-((R)-1'-hydroxy-3'-(trimethylsilyl)prop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate 在 氟化铵 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到(R)-tert-butyl 4-((R)-1'-hydroxyprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  A short route to N-protected furanomycin, 5′-epi-furanomycin and isofuranomycin derivatives

  摘要：

  A short new route to N-protected L-(+)-furanomycin and two of its isomeric derivatives has been developed, which featured the utility of D-serine as a chiral pool material and ring-closing metathesis as a key ring-forming step. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.032

文献信息

• 1,3-diastereocontrol with bromoallenes. Synthesis of enantiomerically pure β-branched α-amino acids
  作者：Fabiana D'Aniello、André Mann、Maurizio Taddei、Camille-Georges Wermuth

  DOI：10.1016/0040-4039(94)80115-0

  日期：1994.10

  Bromoallenes 3a and 3b derived from (D)-Serine undergo SN2′ alkylation with organo copper reagents to give alkynyl amino alcohol derivatives. These compounds can be further transformed into branched enantiometrically enriched α-amino acids as, for example (L)-Isolcucine and (L)-Alloisoleucine.

  衍生自（D）-丝氨酸的溴代烯3a和3b用有机铜试剂进行S N 2'烷基化，得到炔基氨基醇衍生物。这些化合物可以进一步转化为对映体富集的支链α-氨基酸，例如（L）-异亮氨酸和（L）-异苏氨酸。
• On the Substrate Specificity of Dehydration by Lacticin 481 Synthetase
  作者：Xingang Zhang、Wilfred A. van der Donk

  DOI：10.1021/ja067672v

  日期：2007.2.1

  Dehydroamino acids are valuable building blocks that are a challenge to incorporate synthetically into unprotected peptides. Lantibiotic synthetases possess dehydration activity that converts Ser and Thr residues in their peptide substrates into dehydroalanine and dehydrobutyrine residues, respectively. We show here that lacticin 481 synthetase can convert the Thr analogues (R)-3-EtSer, (R)-3-vinylSer, (R)-3-ethynylSer, (R)-3-[(E)-propenyl]Ser, and (R)-3-propynylSer into the corresponding dehydroamino acids when incorporated into its peptide substrate. This relaxed substrate specificity holds promise for using the enzyme for synthetic purposes and for lantibiotic engineering. On the other hand, (R)-3-PrSer, (R)-3-iPrSer, and allo-Thr are not substrates for the enzyme.
• Synthesis and biological evaluation of novel PDMP analogues
  作者：Ulrik Hillaert、Swetlana Boldin-Adamsky、Jef Rozenski、Roger Busson、Anthony H. Futerman、Serge Van Calenbergh

  DOI：10.1016/j.bmc.2006.03.048

  日期：2006.8

  A new series of hybrid PDMP analogues, based both on PDMP and styryl analogues of natural ceramide, has been synthesized from D-serine. The synthetic route was developed such that future introduction of different aryl groups is straightforward. Biological evaluation, both in vitro on rat liver Golgi fractions as well as in HEK-293 and COS-7 cells, revealed two lead compounds with comparable inhibitory potency as PDMP, which could be elaborated to more potent inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.