Synthesis of mannitol hexaacetate

Preparation of mannitol hexaacetate

Preparation of mannitol hexaacetate

Preparation of mannitol hexaacetate

10 g of mannitol, 10 g of fused sodium acetate, and 40 g acetic anhydride are placed in a small flask provided with a reflux condenser and heated to gentle boiling for an hour. The product is poured into water, well stirred and broken up with a glass rod. After some time it is filtered off, washed with water, and recrystallised from alcohol. The yield of mannitol hexaacetate is almost theoretical, colourless crystals; insoluble in water; soluble in hot alcohol; m.p. 119° C.

ystematic organic chemistry, by W. M. Cumming, 259, 1937.

IUPAC Name

[(2R,3R,4R,5R)-2,3,4,5,6-pentaacetyloxyhexyl] acetate

InChI

InChI=1S/C18H26O12/c1-9(19)25-7-15(27-11(3)21)17(29-13(5)23)18(30-14(6)24)16(28-12(4)22)8-26-10(2)20/h15-18H,7-8H2,1-6H3/t15-,16-,17-,18-/m1/s1

InChI Key

NJVBTKVPPOFGAT-BRSBDYLESA-N

Canonical SMILES

CC(=O)OCC(C(C(C(COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Isomeric SMILES

CC(=O)OC[C@H]([C@H]([C@@H]([C@@H](COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Depositor-Supplied Synonyms

642-00-2, D-Mannitol hexaacetate, HEXA-O-ACETYL-D-MANNITOL, SCHEMBL826717, ZINC4403112, 6461AF, AKOS015915917, I14-53976, (2R,3R,4R,5R)-1,2,4,5,6-pentakis(acetyloxy)hexan-3-yl acetate

Removed Synonyms

Mannitol, hexaacetate, CID10288072

IUPAC Name

[(2S,3S,4S,5S)-2,3,4,5,6-pentaacetyloxyhexyl] acetate

InChI

InChI=1S/C18H26O12/c1-9(19)25-7-15(27-11(3)21)17(29-13(5)23)18(30-14(6)24)16(28-12(4)22)8-26-10(2)20/h15-18H,7-8H2,1-6H3/t15-,16-,17-,18-/m0/s1

InChI Key

NJVBTKVPPOFGAT-XSLAGTTESA-N

Canonical SMILES

CC(=O)OCC(C(C(C(COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Isomeric SMILES

CC(=O)OC[C@@H]([C@@H]([C@H]([C@H](COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Depositor-Supplied Synonyms

L-Mannitol hexaacetate

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