A convenient synthesis of the (E)-monoacetates of 2-alkylidenepropane-1,3- diols

Synthesis

Volumn , Issue 17, 2008, Pages 2695-2700

  Miura, Tsuyoshi ^a   Okazaki, Kenjiro ^a   Ogawa, Kyoko ^a   Otomo, Erika ^a   Umetsu, Satoe ^a   Takahashi, Mauko ^a   Kawashima, Yuya ^a   Jyo, Yuki ^a   Koyata, Naka ^a   Murakami, Yasuoki ^a   Imai, Nobuyuki ^a  

^a CHIBA INSTITUTE OF SCIENCE   (Japan)

Author keywords

(E) monoacetates; Acetylation; Diols; Lipase; Regioselectivity

Indexed keywords

METHANOL;

(E)-MONOACETATES; ACETYLATION; DIOLS; EXCELLENT YIELDS; HYDROXY METHYL; LIPASE; PORCINE PANCREATIC LIPASE; REGIOSELECTIVITY; REGIOSPECIFIC; STARTING MATERIALS; TYPE II; VINYL ACETATE;

BYPRODUCTS;

1,3 PROPANEDIOL; 2 (2 FURYLMETHYLENE)PROPANE 1,3 DIOL; 2 (2 METHYLBENZYLIDENE)PROPANE 1,3 DIOL; 2 (2 NAPHTHYLMETHYLENE)PROPANE 1,3 DIOL; 2 (2 THIENYLMETHYLENE)PROPANE 1,3 DIOL; 2 (2,4,6 TRIMETHYLBENZYLIDENE)PROPANE 1,3 DIOL; 2 (3 METHYLBENZYLIDENE)PROPANE 1,3 DIOL; 2 (3 PHENYLPROPYLIDENE)PROPANE 1,3 DIOL; 2 (3 THIENYLMETHYLENE)PROPANE 1,3 DIOL; 2 (4 CHLOROBENZYLIDENE)PROPANE 1,3 DIOL; 2 (4 METHYLBENZYLIDENE)PROPANE 1,3 DIOL; 2 (HYDROXYMETHYL) 3 (2 NAPHTHYL)PROP 2 ENYL ACETATE; 2 (HYDROXYMETHYL) 3 (2 THIENYL)PROP 2 ENYL ACETATE; 2 (HYDROXYMETHYL) 3 (2 TOLYL)PROP 2 ENYL ACETATE; 2 (HYDROXYMETHYL) 3 (3 THIENYL)PROP 2 ENYL ACETATE; 2 (HYDROXYMETHYL) 3 (3 TOLYL)PROP 2 ENYL ACETATE; 2 (HYDROXYMETHYL) 3 (4 METHOXYPHENYL)PROP 3 ENYL ACETATE; 2 (HYDROXYMETHYL) 3 (4 TOLYL)PROP 2 ENYL ACETATE; 2 (HYDROXYMETHYL) 3 [4 (TRIFLUOROMETHYL)PHENYL]PROP 2 ENYL ACETATE; 2 (HYDROXYMETHYL) 3 MESITYLPROP 2 ENYL ACETATE; 2 (HYDROXYMETHYL) 3 PHENYLPROP 2 ENYL ACETATE; 2 (HYDROXYMETHYL) 5 PHENYLPENT 2 ENYL ACETATE; 2 [(ACETYLOXY)METHYL] 5 PHENYLPENT 2 EN 1 YL ACETATE; 2 [4 (TRIFLUOROMETHYL)BENZYLIDENE]PROPANE 1,3 DIOL; 3 (2 FURYL) 2 (HYDROXYMETHYL)PROP 2 ENYL ACETATE; 3 (4 CHLOROPHENYL) 2 (HYDROXYMETHYL)PROP 2 ENYL ACETATE; ACETIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VINYL ACETATE;

ACETYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 51949097067     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067211     Document Type: Article

References (10)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons: New York, 1999.
2. (a) Faber, K. Biotransformations in Organic Chemistry; Springer: Berlin, 2000.
3. (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
4. (a) Hisano, T.; Onodera, K.; Toyabe, Y.; Mase, N.; Yoda, H.; Takabe, K. Tetrahedron Lett. 2005, 46, 6293; and references cited therein.
5. (b) Takabe, K.; Mase, N.; Hisano, T.; Yoda, H. Tetrahedron Lett. 2003, 44, 3267.
6. Miura, T.; Kawashima, Y.; Takahashi, M.; Murakami, Y.; Imai, N. Synth. Commun. 2007, 37, 3105.
7. Miura, T.; Kawashima, Y.; Umetsu, S.; Kanamori, D.; Tsuyama, N.; Jyo, Y.; Murakami, Y.; Imai, N. Chem. Lett. 2007, 36, 814.
8. (a) Gu, J.-X.; Holland, H. L. Synth. Commun. 1998, 28, 3305.
9. (b) Hon, Y.-S.; Lu, L. Tetrahedron 1995, 51, 7937.
10. Cho, J.-H.; Ko, S. Y.; Oh, E.; Park, J. C.; Yoo, J. U. Helv. Chim. Acta 2002, 85, 3994.