Sulfuric Acid → HCID 70360444, compound

Participants

Reaction Steps

In accordance with Flowchart H, D-fructofuranose, pentabenzoate and allyltrimethylsilane are reacted in acetonitrile at reduced temperature, in the presence of borontrifluoride etherate, giving 4,7-anhydro-4-C-[(benzoyloxy)methyl]-1,2,3-trideoxy-D-arabino-oct-1-enitol, 5,6,8-tribenzoate 56, which is reacted with sodium methoxide in methanol, giving 4,7-anhydro-1,2,3-trideoxy-4-C-(hydroxymethyl)-D-manno-oct-1-enitol 57. Compound 57 is reacted with copper sulfate and sulfuric acid in acetone, then neutralized giving 41,1,5:4,7-dianhydro-1,2,3-trideoxy-4-C-[(1-hydroxy-1-methylethoxy)methyl]-6,8-bis-O-(phenylmethyl)-D-manno-oct-1-enitol 58, which is first subjected to ozonolysis in a mixture of pyridine and dichloromethane and then reduced with sodium borohydride in ethanol, giving 3,6:31,4-dianhydro-2-deoxy-3-C-[(1-hydroxy-1-methylethoxy)methyl]-5,7-bis-O-(phenylmethyl)-D-manno-heptitol 59. Compound 59 is hydrogenated in methanol/acetic acid over palladium on carbon, giving 3,6:31,4-dianhydro-2-deoxy-3-C-[(1-hydroxy-1-methylethoxy)methyl]-D-manno-heptitol 60, which is reacted with diphenyl phosphorochloridate in pyridine at reduced temperature, giving the product 3,6:31,4-dianhydro-2-deoxy-3-C-[( 1-hydroxy-1-methylethoxy)methyl]-D-manno-heptitol, 1.7-bis-(diphenyl phosphate) 61, which is hydrogenated in methanol over platinum oxide, giving the product 3,6-anhydro-2-deoxy-3-C-(hydroxymethyl)-D-manno-heptitol, 1,7-bis(dihydrogen phosphate) 62. ##STR21##

Provenance & Evidence