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Tetrahedron: Asymmetry
Volumn 5, Issue 4, 1994, Pages 657-664
Isolation of racemic 2,4-pentanediol and 2,5-hexanediol from commercial mixtures of racemic and meso isomers by way of cyclic sulfites.
Author keywords

[No Author keywords available]
Indexed keywords

2,5 HEXANEDIOL; ALKANEDIOL DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;
EID: 0028314328     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/0957-4166(94)80028-6     Document Type: Article
Times cited : (34)
References (56)
  • 37
    • 33751385008 scopus 로고
    • Another solution to the meso problem is to remove meso-2 from the resolved material by another enzymic resolution:
    • (1993) J. Org. Chem. , vol.58 , pp. 6483-6485
    • Kim1    Lee2
  • 39
    • 0001662239 scopus 로고
    • Whitesell and Reynolds enriched a mixture of meso and racemic 3 by adsorbing meso-3 onto solid calcium chloride (reference 18b). On a preparative scale we found that a 1:1 mixture could be enriched to 3.5:1, but the recovery from this separation was poor (10%) and the enrichment was not increased by a second adsorption. Column chromatography on calcium chloride gave a similar enrichment. Another method for partial separation of the meso isomer was to convert the isomers to their bis(hydrogen phthalate) esters and to wash off the meso ester with hot chloroform:
    • (1968) J. Org. Chem. , vol.33 , pp. 3966-3968
    • Dodson1    Nelson2
  • 43
    • 84908786092 scopus 로고    scopus 로고
    • In six membered sulfites (reference 27) an axial methine oriented syn to the exocyclic oxygen resonates downfield of an axial methine oriented anti to the exocyclic oxygen. Thus, in (±)-4, the 5.14 ppm signal corresponds to the methine proton syn to the oxygen and the 4.32 ppm resonance corresponds lo the methine proton anti to the oxygen. The single resonance in meso-4 occurs at 4.99 ppm, suggests that it is oriented syn to the oxygen. Thus, the methyls are oriented anti to the oxygen.
  • 45
    • 0003481596 scopus 로고
    • M is the specificity constant, 2nd ed., Freeman, New York, The subscripts R and S refer to the enantiomers while subscripts 1 and 2 refer to the first and second substrate, respectively. See ref 21b for details chapter 3
    • (1985) Enzyme Structure and Mechanism
    • Fersht1
  • 52
    • 84908786090 scopus 로고
    • Others have also suggested the open form of a cyclic sulfite ester as reaction intermediates:
    • (1975) Steroids , pp. 29-41
    • Bleile1    Malmberg2    Rowland3

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.