(R)-(+)-isobutyl O-benzyllactate | 121408-94-4

• 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: (R)-(+)-isobutyl O-benzyllactate
• 英文别名: (R)-(+)-Isobutyl-O-benzyllactat；Isobutyl (R)-2-benzyloxypropionate；2-methylpropyl (2R)-2-phenylmethoxypropanoate
• CAS: 121408-94-4
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: PHYPKJSCIMWLNU-GFCCVEGCSA-N

物化性质

• 沸点：
  85-87 °C(Press: 0.001 Torr)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-isobutyl O-benzyllactate 在 lithium aluminium tetrahydride 作用下， 生成 (R)-2-苄氧基-1-丙醇
  参考文献：
  名称：

  Studies on the biodegradation of fosfomycin: Growth of Rhizobium huakuii PMY1 on possible intermediates synthesised chemically

  摘要：

  R. huakuii PMY1 矿化磷霉素的第一步是水解开环，形成 (1R,2R)-1,2-二羟基丙基膦酸。通过化学方法合成了这种膦酸及其三种立体异构体，并测试了它们作为铵盐的矿化作用，Pi 的释放证明了这一点。只有 (1R,2R)-异构体被降解。化学合成了一些膦酸盐，如(±)-1,2-环氧丁基-、(±)-1,2-二羟乙基-、2-氧代丙基-、(S)-2-羟基丙基-、(±)-1-羟基丙基-和(±)-1-羟基-2-氧代丙基膦酸，但没有一种能支持生长。不过，在最后一种膦酸中检测到了体外 C-P 键裂解活性。由于亚磷酸不能用作磷源，因此必须放弃涉及亚磷酸的机制。R. huakuii PMY1 在(R)-和(S)-乳酸和羟基丙酮上生长良好，但在丙酸上生长较差，在丙酮或(R)-和(±)-1,2-丙二醇上生长不良。从(1R,2R)-1,2-二羟基丙基膦酸中释放出的 Pi 在 PO3H2 组中标记了一个氧-18，但在细胞中停留的时间不够长，无法通过酶的转换将 18O 完全交换为 16O。

  DOI：

  10.1039/b821829c
• 作为产物：
  描述：

  (R)-乳酸异丁酯 生成 (R)-(+)-isobutyl O-benzyllactate
  参考文献：
  名称：

  HOPPE, DIETER;TARARA, GERHARD;WILCKENS, MARCUS, SYNTHESIS,(1989) N, C. 83-88

  摘要：

  DOI：

文献信息

• Enantiomerically Pure 2-(Carbamoyloxy)oxiranes and Their Utility in the Synthesis of D- and L-3,6-Dideoxy-3-<i>C</i>-methylhexofuranosides via the Homoaldol Reaction
  作者：Dieter Hoppe、Gerhard Tarara、Marcus Wilckens

  DOI：10.1055/s-1989-27159

  日期：——

  As an example of a novel flexible strategy in the rapid enantioselective construction of branched carbohydrate analogues by the homoaldol reaction, the title compounds were synthesized. α-Metalated (E)-2-butenyl N,N-diisopropylcarbamate is added to (S)- or (R)-2-benzyloxypropanal. The homoaldol adducts are epoxidized; methanolysis affords furanosides of branched 3,6-dideoxyaldohexoses, or, hydrolysis yields the furanoses.

  作为一种新颖的灵活策略示例，通过同醇脱水反应快速选择性构建支链碳水化合物类似物，合成了标题化合物。将α-金属化的(E)-2-丁烯基N,N-二异丙基氨基甲酸酯添加到(S)-或(R)-2-苄氧基丙醛中。生成的同醇脱水加成物经过环氧化处理；甲醇解获得支链3,6-二脱氧醛六糖的呋喃苷，或水解则得呋喃糖。
• Synthetic studies on the rhizoxins. II. An approach to the C10C26 subunit using “substrate directed” allylstannane additions to aldehydes
  作者：Gary E Keck、Kenneth A Savin、Michael A Weglarz、Erik N.K Cressman

  DOI：10.1016/0040-4039(96)00578-3

  日期：1996.5

  The construction of a C10C26 fragment of the 16-membered antitumor macrolide rhizoxin has been achieved in an efficient manner. The central portion of this molecule has been prepared in enantiopure form via an iterative allylstannylation protocol starting with the ester of (R)-lactic acid. The oxazole portion of rhizoxin was attached via a samarium diiodide modified Julia coupling to generate the

  一个C的结构10 C 26的16-元大环内酯抗肿瘤根瘤菌素片段具有以有效的方式实现。该分子的中心部分已通过对映异构纯的形式，从（R）-乳酸的酯开始，通过重复的烯丙基甲磺酰化方法制备。经由二碘化sa改性的Julia偶联连接了根霉菌素的恶唑部分，以产生所需的全部E三烯。
• Enantioselective Synthesis of (+)-(2<i>R</i>,3<i>S</i>,6<i>R</i>)-Decarestrictine L
  作者：Guy Solladié、Eva Arce、Claude Bauder、M. Carmen Carreño

  DOI：10.1021/jo972187r

  日期：1998.4.1

  A convergent enantioselective synthesis of (+)-(2R,3S,6R)-decarestrictine L (1), a natural inhibitor of cholesterol biosynthesis, is described from commercially available (S)-malic acid and (R)-isobutyl lactate. The third chiral center was created by stereoselective reduction of a chiral alpha-hydroxy ketone, and an intramolecular S(N)2-type reaction allowed the stereocontrolled formation of the tetrahydropyranyl ring.
• Markierte Vertreter eines m�glichen Zwischenprodukts der Biosynthese von Fosfomycin inStreptomyces fradiae: Darstellung von (R,S)-(2-Hydroxypropyl)-, (R,S)-, (R)-, (S)-(2-Hydroxy-[1,1-2H2]propyl)-und (R,S)-(2-[18O]Hydroxypropyl)phosphons�ure
  作者：Friedrich Hammerschmidt

  DOI：10.1007/bf00809660

  日期：1991.5

  Racemic methyl O-benzyllactate was reduced to the alcohol, transformed into the bromide and reacted with triethylphosphite to give the diethylphosphonate. Removal of protecting groups afforded a phosphonic acid which was purified as its cyclohexylammonium salt. (S)-Ethyl and (R)-isobutyl O-benzyllactate were reduced with LiAlD4 to the corresponding dideuteriated alcohols, which were transformed in the same way as the racemic compound into the chiral (2-hydroxy-[1,1-H-2(2)]propyl)phosphonic acids. The optical purity of alcohols (S)- and (R)-6b was determined by derivatisation with (+)-MTPA-Cl and H-1-NMR-spectroscopy to be 98%. Exchange of the carbonyl-16-oxygen atom of 2-oxopropylphosphonate for oxygen-18 from (H2O)-O-18, reduction with NaBH4, deprotection and addition of cyclohexylamine yielded the salt (+/-)-18 of (2-[O-18]hydroxy-propyl)phosphonic acid.
• HAMMERSCHMIDT, FRIEDRICH, MONATSH. CHEM., 122,(1991) N, C. 389-398
  作者：HAMMERSCHMIDT, FRIEDRICH

  DOI：——

  日期：——