Synthesis of methyl alpha-D-glucopyranoside (methyl alpha-D-glucoside; alpha-methylglucoside)

Preparation of methyl alpha-D-glucopyranoside

10 ml of absolute methyl alcohol (free from acetone) placed in a flask, which is weighed together with a delivery tube, well cooled, so that no evaporation takes place, and dry hydrogen chloride passed in for a short time. The increase in weight is ascertained and the methyl alcohol diluted with the same solvent until it contains 0.25%, of hydrogen chloride. To 100 g of this dilute hydrogen chloride solution in methanol, 25 g of anhydrous and finely powdered D-glucose are added and boiled with reflux condenser for 45 minutes until the sugar is completely dissolved. The pale yellow liquid is converted into the glucoside on heating to 100° C by placing the solution in a sealed tube and heating for 50 hours in boiling water. The solution is then evaporated to one-third of its volume and well cooled. The methyl alpha-D-glucoside slowly deposits in small, colorless needles, which, after standing over night, are filtered and purified by crystallization from ethyl alcohol. The yield is about 45%.

A Class-Book of Organic Chemistry, by J. B. Cohen, 42, 1919

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol

InChI

InChI=1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3-,4-,5+,6-,7+/m1/s1

InChI Key

HOVAGTYPODGVJG-ZFYZTMLRSA-N

Canonical SMILES

COC1C(C(C(C(O1)CO)O)O)O

Isomeric SMILES

CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

MeSH Synonyms

1-O-methylglucose, alpha-methyl-D-glucopyranoside, alpha-methyl-D-glucoside, alpha-methylglucose, alpha-methylglucoside, alphaMG, beta-methyl-D-glucoside, beta-methylglucoside, methyl alpha-D-glucopyranoside, methyl alpha-D-glucoside, methyl beta-D-glucopyranoside, methyl D-glucopyranoside, methyl-alpha-D-glucoside, methyl-alpha-glucopyranoside, methyl-D-glucoside, methylglucoside, methylglucoside, (alpha-D)-isomer, methylglucoside, (beta-D)-isomer, methylglucoside, 13C-labeled, methylglucoside, 13C-labeled, (beta-D)-isomer, methylglucoside, 2H-labeled, (beta-D)-isomer, methylglucoside, 5-(17)O-labeled, methylglucoside, 6-(13)C-labeled, methylglucoside, 6-(17)O-labeled, (alpha-L)-isomer

Depositor-Supplied Synonyms

Methyl alpha-D-glucopyranoside, Methyl alpha-D-glucoside, Methyl-alpha-D-glucopyranoside, alpha-Methylglucoside, alpha-Methyl-D-glucoside, 97-30-3, alpha-Methyl D-glucose ether, Me alpha-Glc, alpha-D-Methylglucoside, CHEBI:320061, alpha-D-methyl glucoside, alpha-D-Glucoside, methyl, 1-O-methyl-alpha-D-glucoside, alpha-D-Glucopyranoside, methyl, Methyl alpha-D-glucoside (VAN), 1-O-methyl-alpha-D-glucopyranose, HOVAGTYPODGVJG-ZFYZTMLRSA-N, Glucopyranoside, methyl, alpha-D-, 1-O-methyl-alpha-D-glucopyranoside, EINECS 202-571-3, NSC 102101, AI3-18790, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol, .alpha.-Methylglucoside, 25360-06-9, GYP, Methyl .alpha.-D-glucoside, .alpha.-Methyl D-glucose ether, Methyl .alpha.-D-glucopyranoside, Glucopyranoside, methyl, .alpha.-D-, alpha-MDG, Me-alpha-Glc, methyl-D-glucoside, a-methyl-D-glucoside, 1ws4, Methyl hexopyranoside #, DSSTox_CID_6605, Epitope ID:150073, UNII-QCF122NF3R, Methyl ?-D-Glucopyranoside, methyl alpha-D-glucopyranose, DSSTox_RID_78159, Methyl-alpha-D-glucopyranose, QCF122NF3R, DSSTox_GSID_26605, SCHEMBL50473, M9376_SIGMA, .alpha.-Methyl-(d)-glucoside, .alpha.-d-Methylglucopyranoside, AC1L229T, CHEMBL131853, GTPL4640, Methyl -alpha-D-glucopyranoside, 66940_FLUKA, methyl alpha-(D)-glucopyranoside, alpha-methyl-D-glucose pyranoside, MolPort-003-938-545, Tox21_200430, ZINC03861272, alpha-methyl-D-glucopyranoside (AMG), AKOS015896548, MCULE-9257991017, CAS-97-30-3, NCGC00257984-01, AJ-46157, BC681340, K751, KB-297934, LS-180668, FT-0628855, M0228, ST24026180, I06-2478, BE2A51F8-C121-4E44-89AB-05A013F8AA57, 1321-19-3, 15941-70-5, 25281-47-4, 6817-79-4

Removed Synonyms

maltose, Methyl mannoside, Methyl hexopyranoside, Methyl D-glucopyranoside, alpha-Methyl-D-glucopyranoside, .alpha.-D-Glucopyranoside, methyl, CID64947, RW1500, (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)-2-methyltetrahydro-2H-pyran-2,3,4,5-tetraol, mal

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