(2R,3S,4R)-2,3-O-isopropylidene-6-hepten-2,3,4-triol | 106062-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-2,3-O-isopropylidene-6-hepten-2,3,4-triol
• 英文别名: lyxo-Hept-1-ene-4,5,6-triol 5,6-Acetonide；(1R)-1-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol
• CAS: 106062-13-9
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: SANYMDZWSRGGJB-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-2,3-O-isopropylidene-6-hepten-2,3,4-triol 在 水 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 lyxo-4-O-Benzylhept-1-ene-4,5,6-triol
  参考文献：
  名称：

  寡霉素A的AB二糖单元的全合成

  摘要：

  描述了一种有效的（10步，总收率17％），高度非对映选择性的二糖全合成，对应于寡霉素A的AB二糖单元。

  DOI：

  10.1016/s0040-4039(00)84793-0
• 作为产物：
  描述：

  (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde 、 (S,S)-Diethyl tartrate allylboronate 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到(2R,3S,4R)-2,3-O-isopropylidene-6-hepten-2,3,4-triol
  参考文献：
  名称：

  寡霉素A的AB二糖单元的全合成

  摘要：

  描述了一种有效的（10步，总收率17％），高度非对映选择性的二糖全合成，对应于寡霉素A的AB二糖单元。

  DOI：

  10.1016/s0040-4039(00)84793-0

文献信息

• Total synthesis of the AB disaccharide unit of olivomycin A
  作者：William R Roush、Julie A Straub

  DOI：10.1016/s0040-4039(00)84793-0

  日期：1986.1

  An efficient (10 step, 17% overall yield), highly diasteroselective total synthesis of disaccharide , corresponding to the AB disaccharide unit of olivomycin A, is described.

  描述了一种有效的（10步，总收率17％），高度非对映选择性的二糖全合成，对应于寡霉素A的AB二糖单元。
• Indium-mediated allylation of aldehydes: A convenient route to 2-deoxy and 2,6-dideoxy carbohydrates
  作者：Wolfgang H. Binder、Reinhard H. Prenner、Walther Schmid

  DOI：10.1016/s0040-4020(01)80790-0

  日期：1994.1

  The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity. Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated. The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.
• ROUSH, WILLIAM R.;LIN, XIAOFA;STRAUB, JULIE A., J. ORG. CHEM., 56,(1991) N, C. 1649-1655
  作者：ROUSH, WILLIAM R.、LIN, XIAOFA、STRAUB, JULIE A.

  DOI：——

  日期：——
• A highly stereoselective synthesis of the AB disaccharide unit of olivomycin A
  作者：William R. Roush、Xiaofa Lin、Julie A. Straub

  DOI：10.1021/jo00004a054

  日期：1991.2

  A highly stereoselective synthesis of the AB disaccharide (4c) of olivomycin A is described. The synthesis features the double asymmetric allylboration of alpha,beta-dialkoxy aldehyde 8 using tartrate allylboronate (S,S)-9, which provides triol derivative 10 with the correct relative and absolute stereochemistry for utilization in syntheses of the A and B monosaccharides. The derived diol benzyl ether 11 was converted into 3-hydroxy-2-deoxy-lyxo-pyranoside 16 and thioglycoside 18 via the intermediacy of alpha-methyl 2-deoxy-lyxo-pyranoside 14-alpha, and then 16 and 18 were coupled in CH2Cl2 at 23-degrees-C by using Nicolaou's NBS thioglycosidation procedure to give the alpha,alpha-disaccharide 4a with > 6:1 selectivity. Difficulties encountered in the hydrolysis or activation of the methyl glycoside function of 4a prompted the synthesis to be revised by using intermediates containing more easily deprotected anomeric silyl (TBDMS) ethers. Diol 11 was thus selectivity monosilylated to give 21, which was smoothly converted via 2-deoxy-lyxo-pyranose 23 into thioglycoside 18 and 2-deoxypyranoside 27, which possesses a TBMDS protecting group at the anomeric center. Intermediates 18 and 27 were coupled again by using the Nicolaou methodology in a CH3CN-THF cosolvent mixture at -42-degrees-C to give the AB disaccharide TBDMS acetal 4b with greater-than-or-equal-to 20:1 selectivity. Deprotection of the anomeric TBDMS acetal by using Et3NH+F- in CH3CN then completed the synthesis of the olivomycin AB disaccharide unit 4c.