HCID 131716488, compound → HCID 88605173, compound

HRID 2166488Notes

Reaction equation

HRID 2166488 reaction equation
[O:1]([P:8]([O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([CH:10]=[CH:11][C@H:12]1[O:32][C@H:31]([CH2:33][O:34]CC2C=CC=CC=2)[C@@H:22]([O:23]CC2C=CC=CC=2)[C@@H:13]1[O:14]CC1C=CC=CC=1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO.C(O)(=O)C>[O:1]([P:8]([O:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)([CH2:10][CH2:11][C@H:12]1[O:32][C@H:31]([CH2:33][OH:34])[C@@H:22]([OH:23])[C@@H:13]1[OH:14])=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 131716488HCID 131716488, compound

Product 1

HCID 88605173HCID 88605173, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

According to Flowchart C, 2,5-anhydro-D-mannose 24, is protected as the dimethyl acetal 25 which is reacted with sodium hydride in dimethylformamide, followed by benzyl bromide giving 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose, dimethyl acetal 26. Compound 26 is treated with tetrafluoroboric acid in acetonitrile giving 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose 27 which is reacted with diphenyl triphenylphosphoranylidenemethylphosphonate in toluene at reflux, giving 3,6-anhydro-1,2-dideoxy-1-(diphenoxyphosphinyl)-4,5,7-tris-O-(phenylmethyl)-D-manno-hept-1-enitol 28. Compound 28 is hydrogenated over palladium on carbon in methanol and acetic acid, giving 3,6-anhydro-1,2-dideoxy-1-(diphenoxyphosphinyl)-D-manno-heptitol 29, which is reacted with diphenyl chlorophosphate in pyridine, giving 3,6-anhydro-1,2-dideoxy-1-(diphenoxyphosphinyl)-D-manno-heptitol, 7-(diphenyl phosphate) 30, which is then hydrogenated with platinum oxide, giving the product 3,6-anhydro-1,2-dideoxy-1-phosphono-D-manno-heptitol, 7-(dihydrogen phosphate) 31. ##STR11##

Sources & evidence

ORD record
ord-fc1852ce6ca2433fb3256d29cf46ffc6
Source dataset
uspto-grants-1990_07
Patent number
US04945158

Reaction notes

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