Spiro[6H-1,3-dioxolo[4,5-c]pyran-6,5′-oxazolidine]-3′-carboxylic acid, tetrahydro-2,2-dimethyl-2′,7-dioxo-,2-methyl-2-propyl ester, (3aR, 5′S, 7aR)-

Abstract

[319491-89-9] C15H21NO8 (MW 343.33) InChI = 1S/C15H21NO8/c1-13(2,3)23-11(18)16-7-15(24-12(16)19)10(17)9-8(6-20-15)21-14(4,5)22-9/h8-9H,6-7H2,1-5H3/t8-,9-,15+/m1/s1 InChIKey = RZRLSDWFGSKEQD-XWRVAKJBSA-N (ketone catalyst used in the epoxidation of conjugated cis, terminal, trans, trisubstituted, and amphiphilic olefins and in the CH activation of alcohols) Alternate Names: (3aR,5′S,7aR)-tert-butyl 2,2-dimethyl-2′,7-dioxotetrahydrospiro [[1,3]dioxolo[4,5-c]pyran-6,5′-oxazolidine]-3′-carboxylate. Physical Data: white solid; melting point = 139–140 °C;[α]20D = −47.9 (c 0.83, CHCl3) molecular weight = 343.33 g mol−1. 1, 2 Preparative Methods: two literature methods have been reported for the synthesis of ketone 1 from d-glucose using Amadori rearrangement and a series of functional group manipulations.1, 2 Handling, Storage, and Precautions: avoid inhalation and contact with eyes, skin, and clothing. Store in a tightly sealed container. Avoid contact with strong oxidizing agents. Thorough toxicity studies have not been performed. Spiro[6H-1,3-dioxolo[4,5-c]pyran-6,5′-oxazolidine]-3′-carboxylic acid, tetrahydro-2,2-dimethyl-2′,7-dioxo-, methyl ester, (3aR, 5′S, 7aR)- [906371-65-1] C12H15NO8 (MW 301.25) InChI = 1S/C12H15NO8/c1-11(2)19-6-4-18-12(8(14)7(6)20-11)5-13(9(15)17-3)10(16)21-12/h6-7H,4-5H2,1-3H3/t6-,7-,12+/m1/s1 InChIKey = JQXROEASUDOFLI-QHMRUWFYSA-N (ketone catalyst used in stereoselective CH activation of vicinal diols) Alternate Names: (3aR,5′S,7aR)-methyl 2,2-dimethyl-2′,7-dioxotetrahydrospiro [[1,3] dioxolo[4,5-c]pyran-6,5′-oxazolidine]-3′-carboxylate. Physical Data: colorless crystals. Handling, Storage, and Precautions: avoid inhalation and contact with eyes, skin, and clothing. Store in a tightly sealed container. Avoid contact with strong oxidizing agents. Thorough toxicity studies have not been performed. Spiro[6H-1,3-dioxolo[4,5-c]pyran-6,5′-oxazolidine]-3′-carboxylic acid, tetrahydro-2,2-dimethyl-2′,7-dioxo-, ethyl ester, (3aR, 5′S, 7aR)-, [906371-64-0] C13H17NO8 (MW 315.28) InChI = 1S/C13H17NO8/c1-4-18-10(16)14-6-13(22-11(14)17)9(15)8-7(5-19-13)20-12(2,3)21-8/h7-8H,4-6H2,1-3H3/t7-,8-,13+/m1/s1 InChIKey = KYIZCUPXRAOQPJ-RBDZCENOSA-N (ketone catalyst used in stereo selective CH activation of vicinal diols) Alternate Names: (3aR,5′S,7aR)-ethyl 2,2-dimethyl-2′,7-dioxotetrahydrospiro[[1,3]dioxolo[4,5-c]pyran-6,5′-oxazolidine]-3′-carboxylate. Physical Data: colorless crystals. Handling, Storage, and Precautions: avoid inhalation and contact with eyes, skin, and clothing. Store in a tightly sealed container. Avoid contact with strong oxidizing agents. Thorough toxicity studies have not been performed.