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Synlett
Volumn , Issue 3, 2007, Pages 439-442
Direct trifluoroacetylation across a trimethylsilyloxy system as a stereospecific, chemo- and regioselective approach to C3-vicinal halohydrins
Author keywords

1 acyl 3 halo sn glycerols; C3 vicinal halohydrins; Tetra n butylammonium halides; Trifluoroacetic anhydride; Trimethylsilyl ethers
Indexed keywords

1 ACYL 2 O TRIMETHYLSILYL 3 HALOGLYCEROL DERIVATIVE; ACETIC ANHYDRIDE; GLYCEROL DERIVATIVE; HALIDE; TRIFLUOROACETIC ANHYDRIDE; UNCLASSIFIED DRUG;
EID: 33847386666     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-968031     Document Type: Article
Times cited : (3)
References (58)
  • 57
    • 33847419806 scopus 로고    scopus 로고
    • Typical Procedure for the Conversion of the Silyl Ethers 1-4 into the Corresponding Trifluoroacetate Derivatives 5-8 (Step A) To a solution of silyl ether 1-4 (1.00 mmol) and tetra-n-butylammonium halide (2.00 mmol) in alcohol-free CH3Cl (5.0 mL, TFAA (0.278 mL, 2.00 mmol) was added and the reaction system was kept under argon at r.t. for 4-5 h. CH 3Cl and volatile reaction components were evaporated in vacuo, the residue was taken in toluene (5.0 mL) and passed through a pad of silica gel (ca. 5 g) prepared in the same solvent. The support was washed with toluene (ca. 100 mL, fractions containing the target compounds were combined, the eluent was removed under reduced pressure, and the residue was kept under high vacuum at r.t. for 2-3 h to afford trifluoroacetate 5-8 in >90% yields (purity >99% by 1H NMR, 1-Oleoyl-2-trifluoroacetyl-3-chloro- sn-glycerol (5, obtained from 1 0.447 g, 1.00 mmol
    • 4 (355.10): C, 40.59; H, 2.84; Br, 22.50. Found: C, 40.57; H, 2.80; Br, 22.50.
  • 58
    • 33847352055 scopus 로고    scopus 로고
    • Typical Procedure for the Conversion of Trifluoroacetates 5-8 into the Corresponding Halohydrin Derivatives 9-12 (Step B) To a solution of trifluoroacetyl halohydrin 5-8 (1.00 mmol) in pentane-CH 2Cl2 (3:1, v/v, 5.0 mL, a mixture of pyridine (0.8 mL, 10 mmol) and MeOH (10.1 mL, 250 mmol) in the same solvents (5.0 mL) was added at 0°C and the reaction system was left at r.t. for 20 min. Solvents were evaporated under reduced pressure (bath temp. 50°C) and the residue was kept under high vacuum at r.t. for 2-3 h to afford the deprotected haloalkanols 9-12 practically quantitatively (purity >99% by 1H NMR, 1-Oleoyl-3-chloro-sn-glycerol (9, obtained from 5 (0.471 g, 1.00 mmol, Yield 0.375 g (100, colorless oil, Rf, 0.32 (pentane-toluene-EtOAc, 40:50:10, α]D20 +3.00 (c 5.66, CHCl3, Anal. Calcd, ) for C21H 39ClO
    • 3 (259.10): C, 46.36; H, 4.28; Br, 30.84. Found: C, 46.42; H, 4.24; Br, 30.80.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.