SCOPUS 정보 검색 플랫폼

Volumn , Issue 12, 2007, Pages 1966-1968

Efficient regio- and stereoselective synthesis of 1-β-O-glucuronyl carbamates and carbonates from unprotected 1,2,3,4-hydroxyl glucuronates

(3) Thomas, Mickaël a Gesson, Jean Pierre a Papot, Sébastien a

a UNIVERSITÉ DE POITIERS (France)

Author keywords

Carbamate; Carbonate; Glucuronide; Regioselectivity; Stereoselectivity

Indexed keywords

1 BETA O GLUCURONYL CARBAMIC ACID DERIVATIVE; 1,2,3,4 HYDROXYL GLUCURONIC ACID DERIVATIVE; 4 METHYLMORPHOLINE; CARBAMIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; GLUCURONIC ACID; ISOCYANIC ACID DERIVATIVE; MORPHOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 34547634755 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-984534 Document Type: Article

Times cited : (4)

References (13)

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13
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- General Procedure for the Synthesis of 1-β-O- Glucuronyl Carbamates and Carbonates: To a stirred solution of glucuronate 1 (1.5 mmol) and N-methyl-morpholine (5 equiv) in dry MeCN (15 mL) under nitrogen at 0°C was added a solution of either isocyanate or chloroformate (1 mmol in 2 mL of MeCN) over a period of 1 h. The reaction mixture was then allowed to warm to r.t. and stirring was continued for 1 h. The solvent was removed under reduced pressure and the resulting crude product subjected to flash column chromatography. Selected Data Compound 2a: 1H NMR, CD3)2SO, δ, 7.46 (d, 2 H, J, 7.8 Hz, 7.28 (t, 2 H, J, 7.5 Hz, 7.03 (t, 1 H, J, 7.3 Hz, 5.91 (m, 1 H, 5.46 (m, 2 H, 5.37 (m, 2 H, 5.21 (d, 1 H, J, 10.4 Hz, 4.61 (d, 2 H, J, 5.6 Hz, 3.92 (d, 1 H, J, 9.2 Hz, 3.23 (m, 1 H) ppm. 13C NMR, CD3)2SO, δ
- 3): δ = 169.33, 153.85, 97.06, 77.04, 75.38, 74.95, 71.74, 71.08, 52.95, 27.60, 18.88 ppm.

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