Technology Process of benzyl 3,4-di-O-benzyl-6,7-dideoxy-2-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside
There total 10 articles about benzyl 3,4-di-O-benzyl-6,7-dideoxy-2-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Methyltriphenylphosphonium bromide;
With
sodium hexamethyldisilazane;
In
tetrahydrofuran;
at 20 ℃;
for 0.5h;
(2S,3S,4S,5R,6S)-3,4,6-Tris-benzyloxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde;
at 20 ℃;
for 1.5h;
Multistep reaction. Further stages.;
DOI:10.1021/ja028386w
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: AcCl / 96 h / 20 - 50 °C
1.2: 10 percent / p-TsOH monohydrate / dimethylformamide / 1 h / Heating
2.1: Bu2SnO / toluene; methanol / 3 h / Heating
2.2: 89 percent / TEA / toluene / 3 h / 20 °C
3.1: 88 percent / Ba(OH)2 hydrate; BaO / dimethylformamide / 5 h / 20 °C
4.1: 82 percent / NaBH4 / dimethylsulfoxide / 20 h / 140 °C
5.1: 94 percent / tetrabutylammonium bromide; NaH / dimethylformamide / 2 h / 20 °C
6.1: 88 percent / BH3*THF; Bu2BOTf / tetrahydrofuran; diethyl ether / 1 h / 0 °C
7.1: (CO)2Cl2; DMSO; TEA / CH2Cl2 / -78 - 20 °C
8.1: NaHMDS / tetrahydrofuran / 0.5 h / 20 °C
8.2: 80 percent / 1.5 h / 20 °C
With
barium dihydroxide; sodium tetrahydroborate; borane-THF; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; TEA; tetrabutylammomium bromide; sodium hexamethyldisilazane; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; acetyl chloride; barium(II) oxide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
7.1: Swern oxidation;
DOI:10.1021/ja028386w
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: AcCl / 96 h / 20 - 50 °C
1.2: 10 percent / p-TsOH monohydrate / dimethylformamide / 1 h / Heating
2.1: Bu2SnO / toluene; methanol / 3 h / Heating
2.2: 89 percent / TEA / toluene / 3 h / 20 °C
3.1: 88 percent / Ba(OH)2 hydrate; BaO / dimethylformamide / 5 h / 20 °C
4.1: 82 percent / NaBH4 / dimethylsulfoxide / 20 h / 140 °C
5.1: 94 percent / tetrabutylammonium bromide; NaH / dimethylformamide / 2 h / 20 °C
6.1: 88 percent / BH3*THF; Bu2BOTf / tetrahydrofuran; diethyl ether / 1 h / 0 °C
7.1: (CO)2Cl2; DMSO; TEA / CH2Cl2 / -78 - 20 °C
8.1: NaHMDS / tetrahydrofuran / 0.5 h / 20 °C
8.2: 80 percent / 1.5 h / 20 °C
With
barium dihydroxide; sodium tetrahydroborate; borane-THF; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; TEA; tetrabutylammomium bromide; sodium hexamethyldisilazane; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; acetyl chloride; barium(II) oxide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
7.1: Swern oxidation;
DOI:10.1021/ja028386w
