Novel diastereoselective acylation of 4-C-hydroxymethyl-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-α-D-pentofurano se: Effect of lipases and acylating agents on stereoselectivity

Tetrahedron Letters

Volumn 40, Issue 51, 1999, Pages 9145-9146

  Sharma, Sunil K ^a   Roy, Sucharita ^a   Kumar, Rajesh ^a   Parmar, Virinder S ^a  

^a UNIVERSITY OF DELHI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

4C HYDROXYMETHYL 1,2 O 1 METHYLETHYLIDENE 3 O PHENYLMETHYL ALPHA D PENTOFURANOSE; CARBOHYDRATE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; BURKHOLDERIA CEPACIA; CANDIDA; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHIRALITY; NONHUMAN; PARTIAL DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

BURKHOLDERIA; BURKHOLDERIA CEPACIA; CANDIDA; NEGIBACTERIA;

EID: 0033579612     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01942-5     Document Type: Article

References (10)

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4. Wengel, J. Acc. Chem. Res. 1999, 32, 301 and references cited therein.
5. (a) Parmar, V.S.; Prasad, A.K.; Sharma, N.K.; Singh, S.K.; Pati, H.N.; Gupta, S. Tetrahedron 1992, 48, 6495.
6. (b) Bisht, K.S.; Tyagi, O.D.; Prasad, A.K.; Sharma, N.K. Gupta, S.; Parmar, V.S. Bioorg. Med. Chem. 1994, 2, 1015.
7. (c) Bisht, K.S.; Kumar, A.; Kumar, N.; Parmar, V.S. Pure Appl. Chem. 1996, 68, 749.
8. (d) Bisht, K.S.; Parmar, V.S.; Crout, D.H.G. Tetrahedron:Asymmetry 1993, 4, 957.
9. (e) Parmar, V.S.; Prasad, A.K.; Pati, H.N.; Kumar, R.; Azim, A.; Roy, S.; Errington, W. Bioorg. Chem. 1999, 27, 119.
10. General procedure: The diol 1 (100 mg) was incubated with the lipase (30 mg) in organic solvents (PPL/THF, CRL/DIPE, Amano PS/THF and CAL/DIPE) along with equimolar amount of the acylating agent in a controlled-temperature rotary shaker at 40-42°C. The reaction was monitored by HPLC and quenched by filtering off the enzyme followed by solvent evaporation at reduced pressure. The residue was chromatographed on silica to yield the acylated compound.