Technology Process of Methanesulfonic acid (3aS,4R,6R,7R,7aS)-7-azido-6-[(1R,2R,3S,4R,5R)-3-benzyloxy-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester
There total 14 articles about Methanesulfonic acid (3aS,4R,6R,7R,7aS)-7-azido-6-[(1R,2R,3S,4R,5R)-3-benzyloxy-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester which
guide to synthetic route it.
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synthetic route:
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110403-97-9
Methanesulfonic acid (3aS,4R,6R,7R,7aS)-7-azido-6-[(1R,2R,3S,4R,5R)-3-benzyloxy-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester
- Guidance literature:
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Multi-step reaction with 5 steps
1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 6 h / Ambient temperature
2: sodium azide; ammonium chloride / ethanol / 11 h / 80 - 90 °C
3: sodium tetrahydroborate; sodium acetate; acetic anhydride / 1.) DMSO a) 12 h, RT. b) 3 h, 0 deg C 2.) dichloromethane-ethanol-water, 0 deg C, 30 min
4: toluene-4-sulfonic acid; acetic acid / 1.) 80-90 deg C, 3 h 2.) acetone, RT, 2 d
5: pyridine / dichloromethane / Ambient temperature
With
pyridine; sodium tetrahydroborate; sodium azide; ammonium chloride; sodium acetate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid;
In
tetrahydrofuran; ethanol; dichloromethane;
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110403-97-9
Methanesulfonic acid (3aS,4R,6R,7R,7aS)-7-azido-6-[(1R,2R,3S,4R,5R)-3-benzyloxy-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester
- Guidance literature:
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Multi-step reaction with 12 steps
1: pyridine / Ambient temperature
2: potassium fluoride; tetraethylammonium chloride / water; acetonitrile / 6 h / Ambient temperature
3: pyridine / 16 h / 0 °C
4: sodium methylate / tetrahydrofuran; methanol / 1 h / Ambient temperature
5: pyridine / dichloromethane / 9 h / 0 °C
6: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / -15 - -10 °C
7: sodium methylate / methanol; dichloromethane / 72 h / 0 °C
8: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 6 h / Ambient temperature
9: sodium azide; ammonium chloride / ethanol / 11 h / 80 - 90 °C
10: sodium tetrahydroborate; sodium acetate; acetic anhydride / 1.) DMSO a) 12 h, RT. b) 3 h, 0 deg C 2.) dichloromethane-ethanol-water, 0 deg C, 30 min
11: toluene-4-sulfonic acid; acetic acid / 1.) 80-90 deg C, 3 h 2.) acetone, RT, 2 d
12: pyridine / dichloromethane / Ambient temperature
With
pyridine; potassium fluoride; sodium hydroxide; sodium tetrahydroborate; sodium azide; ammonium chloride; tetraethylammonium chloride; sodium methylate; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; acetonitrile;
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110403-97-9
Methanesulfonic acid (3aS,4R,6R,7R,7aS)-7-azido-6-[(1R,2R,3S,4R,5R)-3-benzyloxy-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester
- Guidance literature:
-
Multi-step reaction with 4 steps
1: sodium azide; ammonium chloride / ethanol / 11 h / 80 - 90 °C
2: sodium tetrahydroborate; sodium acetate; acetic anhydride / 1.) DMSO a) 12 h, RT. b) 3 h, 0 deg C 2.) dichloromethane-ethanol-water, 0 deg C, 30 min
3: toluene-4-sulfonic acid; acetic acid / 1.) 80-90 deg C, 3 h 2.) acetone, RT, 2 d
4: pyridine / dichloromethane / Ambient temperature
With
pyridine; sodium tetrahydroborate; sodium azide; ammonium chloride; sodium acetate; acetic anhydride; toluene-4-sulfonic acid; acetic acid;
In
ethanol; dichloromethane;