SCOPUS 정보 검색 플랫폼

Volumn 29, Issue 1, 1988, Pages 37-40

A convenient synthesis of 5-substituted-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-ones via a chemoselective differentiation of the two ester functions of dimethyl acetonedicarboxylate

(2) Prugh, John D a Deana, Albert A a

a MERCK RESEARCH LABORATORIES (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,4,5,6 TETRAHYDRO 4 HYDROXY 2H PYRAN 2 ONE DERIVATIVE; UNCLASSIFIED DRUG;

DRUG DEVELOPMENT; METHODOLOGY; NONHUMAN; PRELIMINARY COMMUNICATION;

EID: 0023873361 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(88)80010-8 Document Type: Article

Times cited : (13)

References (10)

1
- 0001010871
- (1973) Advances in Enzymology , pp. 373
- Rodwell¹ McNamara² Shapiro³

2
- 0022601104
- and references cited therein
- (1986) J. Org. Chem. , vol.51 , pp. 648
- Prugh¹ Rooney² Deana³ Ramjit⁴

3
- 0022444094
- and references cited therein
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 4586
- Hecker¹ Heathcock²

4
- 84919146160
- 3) δ 2.83 (1H, q); 3.05 (1H, d); 3.12 (1H, d); 3.55 (3H, s); 3.62 (3H, s); 3.66 (3H, s); 3.68 (3H, s); 4.17 (2H, d); 4.33 (1H, m); 4.68 (1H, s); 4.70 (1H, s); 5.54 (1H, t); (5.81(1H, m); 7.0–7.4 (1DH, m)3a (Z, E mixture) δ 1.64 (1H, t); 1.96 (1H, t); 2.19 (H, S); 2.68 (1H, dd) 2.78 (H, dd); 3.8 (2H, m); 3.6 (3H, s); 3.64 (3H, 5); 3.66 (3H, s); 3.68 (3H, s) 3.84 (1H, m); 4.15–4.31 [[Truncated]]

5
- 84919146159
- Unpublished results obtained in this laboratory.

6
- 84919146158
- 4, (6g, 0.159 mole) was added in small portions over a 6 hour period to a stirred solution of 2 (7.3 mmole) in methanol THF (1:1;v:v;100 mL) at ice-water bath temperature. The reaction was worked up and resubmitted to the reduction conditions when TLC showed the reaction to be incomplete. TLC is used to monitor completion of the reaction.

7
- 0004175094
- Benjamin
- (1962) Hydroboration , pp. 245
- Brown¹

8
- 84919146157
- 4 and other reducing reagents, and as the ion is unreactive toward reduction.

9
- 84919146156
- 3) δ 2.25 (1H, m) 2.6–2.8 (4H, m); 4.22 (1H, DD, J = 5 Hz, 11 Hz); 4.46 (1H, t, J = 11 Hz); 7.15–7.45 (5 H, m) 8a, mp = 89–91°C, 96, gum; 86, 163–165°C; 9b, 136–138°C. All new compounds gave satisfactory NMR spectral data, microanalysis and/or mass spectra except for the mixture 5 where only NMR was obtained.

10
- 0009881781
- (1975) Tetrahedron Lett. , pp. 687
- Danneels¹ Anteunis²

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