Dimethylformamide → HCID 12756307、化合物

反応式

CO[C@H:3]1O[C@H:7]([CH2:9]O)[C@@H:6](O)[C@H:5](O)[C@H:4]1O.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN([CH:37]=[O:38])C>>[C:14]([O:38][C:37]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[CH:9]=[CH:7][CH:6]=[CH:5][CH:4]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

反応物 3

HCID 6228Dimethylformamide

HCID 6456Trityl chloride

HCID 64947methyl alpha-D-glucopyranoside

生成物 1

HCID 12756307HCID 12756307、化合物

実験手順

A process of producing compound 6 (methyl-2,3,4-trideoxy-6-O-trityl-4-methylcarboxymethyl-hex-2-enpyranoside) comprising reacting compound 1 (methyl-α-D-glucopyranoside) in the presence of Ph3CCl and 4-Me2Py and DMF to produce compound 2 (6-O-trityl-α-methylglucoside) and reacting compound 2 in the presence of n-Bu2SnO, CH3OH and BzCl, Et3N, THF to produce compound 3 (methyl-2-O-benzoyl-6-O-trityl-α-D-glucopyranoside) and reacting compound 3 in the presence of MsCl and Et3N, CH2Cl2 to produce compound 4 (methyl-2-O-benzoyl-3,4-di-O-methanesulfonyl-6-O-trityl-α-D-glucopyranoside) and reacting compound 4 in the presence of Zn-Cu, DMF and CH3ONa/CH3OH to produce compound 5 (methyl-3,4-dideoxy-6-O-trityl-hex-3-enpyranoside) and reacting compound 5 in the presence of CH3C(OCH3)3, C2H5CO2H while refluxing xylenes to produce the desired compound 6 (methyl-2,3,4-trideoxy-6-O-trityl-4-methylcarboxymethyl-hex-2-enpyranoside).

出典と根拠

ORDレコード: ord-385063d010214c269ff2e25cad85c402
出典データセット: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04256646

反応ノート

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