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Volumn , Issue 13, 2008, Pages 2036-2040

Straightforward and efficient synthesis of (4R,6S)-4-(tert-butyldimethyl- siloxy)-6-(hydroxymethyl)tetrahydropyran-2-one

Author keywords

Drugs; Homogeneous catalysis; Lactones; Stereoselective synthesis; Tin

Indexed keywords

3 HYDROXYBUTYRIC ACID; 4 (TERT BUTYLDIMETHYLSILOXY) 6 (HYDROXYMETHYL)TETRAHYDROPYRAN 2 ONE; ACETIC ACID ESTER; ETHYL 4 CHLORO 3 HYDROXYBUTYRIC ACID; LACTONE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; TIN;

EID: 49649100687     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077957     Document Type: Article
Times cited : (21)

References (33)
  • 7
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    • For examples of synthesis, see: Fernandes, R. A, Kumar, P. Eur. J. Org. Chem. 2002, 2921; and references cited therein
    • For examples of synthesis, see: Fernandes, R. A.; Kumar, P. Eur. J. Org. Chem. 2002, 2921; and references cited therein.
  • 13
    • 0021702015 scopus 로고    scopus 로고
    • Lactone 1 (P = TBS) with mp 74-75 °C was obtained in seven steps from (S)-malic acid ester via (S)-butane-1,2,4-triol in an overall yield of 2%: Rosen, T.; Taschner, M. J.; Heathcock, C. H. J. Org. Chem. 1984, 49, 3994.
    • Lactone 1 (P = TBS) with mp 74-75 °C was obtained in seven steps from (S)-malic acid ester via (S)-butane-1,2,4-triol in an overall yield of 2%: Rosen, T.; Taschner, M. J.; Heathcock, C. H. J. Org. Chem. 1984, 49, 3994.
  • 14
    • 49649103874 scopus 로고    scopus 로고
    • D -7.5 and mp 72-74 °C was accessed in 10% overall yield by an eight-step convergent synthesis based on diastereoselective aldol condensation between enzymatically derived chiral sulfoxide auxiliary prepared in two steps and chiral building block derived from (S)-butane-1,2,4-triol: Tang, J.; Brackenridge, I.; Roberts, S. M.; Beecher, J.; Willetts, A. J. Tetrahedron 1995, 57, 13217.
    • D -7.5 and mp 72-74 °C was accessed in 10% overall yield by an eight-step convergent synthesis based on diastereoselective aldol condensation between enzymatically derived chiral sulfoxide auxiliary prepared in two steps and chiral building block derived from (S)-butane-1,2,4-triol: Tang, J.; Brackenridge, I.; Roberts, S. M.; Beecher, J.; Willetts, A. J. Tetrahedron 1995, 57, 13217.
  • 15
    • 0035812832 scopus 로고    scopus 로고
    • D +1.9 and mp 95 °C in nine steps and in 13% overall yield: (a) Ghorpade, S. R.; Kalkote, U. R.; Chavan, S. P.; Bhide, S. R.; Ravindranathan, T.; Puranik, V. G. J. Org. Chem. 2001, 66, 6803.
    • D +1.9 and mp 95 °C in nine steps and in 13% overall yield: (a) Ghorpade, S. R.; Kalkote, U. R.; Chavan, S. P.; Bhide, S. R.; Ravindranathan, T.; Puranik, V. G. J. Org. Chem. 2001, 66, 6803.
  • 17
    • 33845929620 scopus 로고    scopus 로고
    • D +0.33, mp 96-98 °C in seven steps in 16% overall yield: Tararov, V. I.; Andrushko, N.; Andrushko, V.; König, G.; Spannenberg, A.; Börner, A. Eur. J. Org. Chem. 2006, 5543; and references cited therein.
    • D +0.33, mp 96-98 °C in seven steps in 16% overall yield: Tararov, V. I.; Andrushko, N.; Andrushko, V.; König, G.; Spannenberg, A.; Börner, A. Eur. J. Org. Chem. 2006, 5543; and references cited therein.
  • 20
    • 0037053889 scopus 로고    scopus 로고
    • A hint for the preparation of acid 8 from ester 7 with LiOH in 70% yield was given in: Kobayashi, Y.; Wang, Y.-G. Tetrahedron Lett. 2002, 43, 4381.
    • A hint for the preparation of acid 8 from ester 7 with LiOH in 70% yield was given in: Kobayashi, Y.; Wang, Y.-G. Tetrahedron Lett. 2002, 43, 4381.
  • 21
    • 0011242466 scopus 로고
    • and references cited therein
    • (a) Epstein, W. W.; Sweat, F. W. Chem. Rev. 1967, 67, 247; and references cited therein.
    • (1967) Chem. Rev , vol.67 , pp. 247
    • Epstein, W.W.1    Sweat, F.W.2
  • 29
    • 49649102440 scopus 로고    scopus 로고
    • 3).
    • 3).
  • 31
    • 49649091392 scopus 로고    scopus 로고
    • Procedure for the Preparation of, 2S,4R, 4-(tert-Butyldimethylsiloxy)-6-oxotetrahydro-2H-pyran-2-yl]methyl Acetate (11) To the solution of (4R,6S)-4-(tert-butyldimethylsiloxy)-6-(iodomethyl, tetrahydropyran-2-one (2, 40.00 g, 108.0 mmol) in AcOH (660 mL) was added AgOAc (20.03 g, 118.8 mmol, The resultant mixture was then heated at 120-125 °C for 6 h. The reaction mixture was filtered through diatomite filter medium (Celite®, The obtained filtrate was evaporated to afford the residue. To this residue EtOAc (500 mL) and H2O (600 mL) were added. The organic layer was separated and the aqueous layer was washed again with EtOAc (5 × 150 mL, The combined organic layers were washed with H2O (4 × 300 mL, brine (5 × 300 mL) and dried over anhyd MgSO4, filtered, and concentrated under reduced pressure to afford 30.28 g 92.6, of, 2S
    • 3).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.