Sodium hydride → Mannitol

HRID 2166489Notes

Reaction equation

HRID 2166489 reaction equation
C(O)[CH:2]([OH:13])[CH:3]([OH:12])[CH:4]([OH:11])[CH:5]([OH:10])[CH:6]([OH:9])[CH:7]=[O:8].[H-].[Na+]>C(COC)OC>[CH2:2]([OH:13])[C@H:3]([C@H:4]([C@@H:5]([C@@H:6]([CH2:7][OH:8])[OH:9])[OH:10])[OH:11])[OH:12]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 219662glycero-galacto-Heptose

Product 1

HCID 6251Mannitol

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In Method B, 3,6-anhydro-2-deoxy-4,5,7-tris-O-(phenylmethyl)-D-gluco (and D-manno) heptose mixture 4 is reacted with a tetrasubstituted bisphosphonate, where and R' and R" may be any of the aliphatic substituents listed in Table II, and sodium hydride in dimethoxy ethane, giving the isomeric mixture 2,5-anhydro-1-deoxy-1-C-(disubstituted phosphinyl)-3,4,6-tris-O-(phenylmethyl)-D-glucitol and D-mannitol 12' which are then reacted as described in Method A giving 2,5-anhydro-1-deoxy 1-(disubstituted phosphinyl)-D-mannitol, 6-(disubstituted phosphate) 14' and the corresponding D-glucitol derivative 23'. ##STR16##

Sources & evidence

ORD record
ord-3702fd2c93d743779c57694b458e9000
Source dataset
uspto-grants-1990_07
Patent number
US04945158

Reaction notes

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