Reaktion #51786

ord-756be44ab8d44c84a839446504c2df29

Reaktionsgleichung

CC(C)C1(CCc2csc(CO)c2)CC(O)=CC(=O)O1
4-hydroxy-6-[2-(5-hydroxymethyl-thiophen-3-yl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one
Cc1ccc(S(=O)(=O)Sc2cc(C)c(CO)cc2C(C)(C)C)cc1
toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
Cc1cc(SC2=C(O)CC(CCc3csc(CO)c3)(C(C)C)OC2=O)c(C(C)(C)C)cc1CO
title compound
Cc1cc(SC2=C(O)CC(CCc3csc(CO)c3)(C(C)C)OC2=O)c(C(C)(C)C)cc1CO
3-(2-tert-Butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-[2-(5-hydroxymethyl-thiophen-3-yl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

Edukte

CC(C)C1(CCc2csc(CO)c2)CC(O)=CC(=O)O1
4-hydroxy-6-[2-(5-hydroxymethyl-thiophen-3-yl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one
Cc1ccc(S(=O)(=O)Sc2cc(C)c(CO)cc2C(C)(C)C)cc1
toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The title compound was prepared as described in General Method 16a using 4-hydroxy-6-[2-(5-hydroxymethyl-thiophen-3-yl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one (Example E-23; 0.67 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester (Example BB-2; 0.74 mmol), potassium carbonate (2.7 mmol) in DMF (5 mL), mp 76-80° C. MS (APCI): 503 (M−H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06852711B2uspto-grants-2005_02