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Journal of Combinatorial Chemistry
Volumn 9, Issue 3, 2007, Pages 366-369
Solid-phase synthesis of sn-1,2- And sn-2,3-diacylglycerols via ring-opening of the glycidyl-bound resin
Author keywords

[No Author keywords available]
Indexed keywords

CARBOXYLIC ACID; DIACYLGLYCEROL; EPOXY RESIN;
EID: 34249936754     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc060139r     Document Type: Article
Times cited : (6)
References (35)
  • 23
    • 13544271031 scopus 로고    scopus 로고
    • Hwang, J. Y.; Choi, H.-S.; Lee, D.-H.; Yoo, S.-e; Gong, Y.-D. J. Comb. Chem. 2005, 1, 136.
    • (d) Hwang, J. Y.; Choi, H.-S.; Lee, D.-H.; Yoo, S.-e; Gong, Y.-D. J. Comb. Chem. 2005, 1, 136.
  • 26
    • 0141795495 scopus 로고    scopus 로고
    • Gong. Y.-D.; Seo, J.-s.; Chon, Y.-S.; Hwang, J.-Y.; Park, J.-Y.; Yoo, S.-e. J. Comb. Chem. 2003, 5, 577.
    • (g) Gong. Y.-D.; Seo, J.-s.; Chon, Y.-S.; Hwang, J.-Y.; Park, J.-Y.; Yoo, S.-e. J. Comb. Chem. 2003, 5, 577.
  • 34
    • 34249943230 scopus 로고    scopus 로고
    • General procedure for the synthesis of 8a. To a suspension of 2-chlorotrityl chloride resin 1 (5 g, 6.5 mmol, 1.3 mmol g-1) in dry DCM (50 mL) was added TEA (5.6 ml, 40 mmol, followed by the slow addition of (S)-glycidol (2.7 ml, 40 mmol) in dry DCM at 0 °C. The suspension was shaken for 48 h at room temperature under an argon atmosphere. The glycidyl-bound resin 3 was filtered, washed with DMF (2 × 100 mL, DCM (2 × 100 mL, and MeOH (2 × 100 mL, and dried under high vacuum. The glycidyl bound resin 3 (2.0 g, 2.6 mmol) was suspended in dry DMF (30 mL, and TBAB (83 mg, 0.26 mmol) and palmitic acid (6.7 g, 26.0 mmol) were successively added. The mixture was shaken for 16 h at 90 °C. The polymer-bound monoacylglycerol resin 5a was filtered, washed with DMF (2 × 100 mL, DCM (2 × 100 mL, and MeOH (2 × 100 mL, and dried under high vacuum. The polymer-bound monoacylglycerol resin 5a (100 mg, 0.13 mmol) was swollen in DMF (4 mL) and
    • 3): δ 7.50 (m, 2H), 7.41 (m, 3H), 5.31 (m, 1H), 4.59 (dd, 1H, J = 11.9 Hz, J = 3.8 Hz), 4.36 (dd, 1H, J = 11.9 Hz, J = 5.5 Hz), 4.26 (dd, 1H, J = 11.9 Hz, J = 4.7 Hz), 4.12 (dd, 1H, J = 11.9 Hz, J = 5.8 Hz), 3.54 and 3.53 (s, 3H), 2.31 -2.26 (m, 4H), 1.60-1.54 (m, 4H), 1.32-1.25 (m, 26H), 0.91-0.87 (m, 6H).
  • 35
    • 34249946871 scopus 로고    scopus 로고
    • General procedure for the synthesis of 10a. The polymer-bound monoacylglycerol resin 5 (100 mg, 0.13 mmol) was swollen in THF/DCM (1:1, 4 mL, followed by the addition of diisopropyl azodicaroxylate (0.13 mL, 0.65 mmol, triphenylphosphine (170 mg, 0.65 mmol, and valeric acid (0.07 mL, 0.65 mmol, After the reaction was shaken for 12 h at room temperature, the polymer-bound diacylglycerol resin 9a was filtered, washed with DMF (2 × 20 mL, DCM (2 × 20 mL, and MeOH (2 × 20 mL, and dried under high vacuum. To the polymer-bound diacylglycerol resin 9a (100 mg, 0.13 mmol) in DCM (4 mL) was added boron trichloride (0.65 mL, 0.65 mmol, 1.0 M in DCM) at -20 °C for 1 h. The reaction mixture was poured into a saturated NaHCO3 solution, and the organic layer was concentrated. Purification by column chromatography gave the corresponding desired product, hexadecanoic acid 3-hydroxy-2- pentanoyloxy-propyl ester (10a, α]D: +2.88 c, 0.33, CHCl
    • 3).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.