Technology Process of Benzoic acid (3aS,5S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester
There total 1 articles about Benzoic acid (3aS,5S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
5-O-benzoyl-1,2-O-isopropylidene-α-L-ribofuranose;
With
sodium hydride;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 1h;
benzyl bromide;
With
tetra-(n-butyl)ammonium iodide;
In
tetrahydrofuran;
at 0 - 20 ℃;
Further stages.;
DOI:10.1021/ol0168059
- Guidance literature:
-
Multi-step reaction with 6 steps
1: aq. HCl / dioxane; methanol / 1.5 h / 20 °C
2: DMAP / toluene / 3 h / 90 °C
3: Bu3SnH; AIBN / 1 h / Heating
4: 60 percent / H2 / Pd/C / ethanol / 72 h / 20 °C / 2844.39 Torr
5: 88 percent / CrO3; pyridine; Ac2O / CH2Cl2 / 0.25 h / 20 °C
6: 66 percent / DAST / CH2Cl2 / 36 h / Heating
With
pyridine; chromium(VI) oxide; hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; acetic anhydride; 4,4'-diaminostilbene-2,2'-disulfonic acid;
palladium on activated charcoal;
In
1,4-dioxane; methanol; ethanol; dichloromethane; toluene;
DOI:10.1021/ol0168059
- Guidance literature:
-
Multi-step reaction with 7 steps
1: aq. HCl / dioxane; methanol / 1.5 h / 20 °C
2: DMAP / toluene / 3 h / 90 °C
3: Bu3SnH; AIBN / 1 h / Heating
4: 60 percent / H2 / Pd/C / ethanol / 72 h / 20 °C / 2844.39 Torr
5: 88 percent / CrO3; pyridine; Ac2O / CH2Cl2 / 0.25 h / 20 °C
6: 66 percent / DAST / CH2Cl2 / 36 h / Heating
7: H2SO4 conc. / acetic acid / 0.08 h / 0 °C
With
pyridine; chromium(VI) oxide; hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); sulfuric acid; hydrogen; tri-n-butyl-tin hydride; acetic anhydride; 4,4'-diaminostilbene-2,2'-disulfonic acid;
palladium on activated charcoal;
In
1,4-dioxane; methanol; ethanol; dichloromethane; acetic acid; toluene;
DOI:10.1021/ol0168059
