Technology Process of (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-19a-methylhexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin
There total 11 articles about (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-19a-methylhexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
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1415891-57-4
(2R,3S,4aR,5aS,6aR,10aS,11aR,13aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-11a-methoxytetradecahydro-2H-pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepine
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1415891-45-0
(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-19a-methylhexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin
- Guidance literature:
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Multi-step reaction with 13 steps
1: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
2: hydrogen; 10 wt% Pd(OH)2 on carbon / ethyl acetate / 18 h / 20 °C
3: 2,6-dimethylpyridine / tetrahydrofuran / 0.5 h / -80 °C / Inert atmosphere
4: tetrahydrofuran / 0.67 h / -80 °C / Inert atmosphere
5: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; hexane / -100 °C / Inert atmosphere
6: toluene-4-sulfonic acid / dichloromethane; methanol / 1 h / 20 °C / Inert atmosphere
7: magnesium bromide diethyl etherate; lithium bromide / dichloromethane / 2.5 h / -15 - -5 °C
8: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 20 °C
9: toluene-4-sulfonic acid / methanol; 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
10: flash chromatography
11: zinc trifluoromethanesulfonate / dichloromethane; nitromethane / 12 h / 20 °C / Inert atmosphere
12: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
13: dichloromethane; n-heptane / 0 - 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; triethylsilane; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; 10 wt% Pd(OH)2 on carbon; hydrogen; magnesium bromide diethyl etherate; zinc trifluoromethanesulfonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; lithium bromide;
In
tetrahydrofuran; methanol; nitromethane; hexane; n-heptane; dichloromethane; ethyl acetate; 1,2-dichloro-ethane;
DOI:10.1021/jo302267f
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1415891-45-0
(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-19a-methylhexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin
- Guidance literature:
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Multi-step reaction with 10 steps
1: potassium tert-butylate; tert.-butylhydroperoxide / tetrahydrofuran / -78 - -25 °C / Inert atmosphere
2: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; hexane / -100 °C / Inert atmosphere
3: toluene-4-sulfonic acid / dichloromethane; methanol / 1 h / 20 °C / Inert atmosphere
4: magnesium bromide diethyl etherate; lithium bromide / dichloromethane / 2.5 h / -15 - -5 °C
5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 20 °C
6: toluene-4-sulfonic acid / methanol; 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
7: flash chromatography
8: zinc trifluoromethanesulfonate / dichloromethane; nitromethane / 12 h / 20 °C / Inert atmosphere
9: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
10: dichloromethane; n-heptane / 0 - 20 °C / Inert atmosphere
With
tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; potassium tert-butylate; magnesium bromide diethyl etherate; zinc trifluoromethanesulfonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; lithium bromide;
In
tetrahydrofuran; methanol; nitromethane; hexane; n-heptane; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/jo302267f
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1415891-45-0
(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-19a-methylhexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin
- Guidance literature:
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Multi-step reaction with 10 steps
1: tetrahydrofuran / 0.67 h / -80 °C / Inert atmosphere
2: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; hexane / -100 °C / Inert atmosphere
3: toluene-4-sulfonic acid / dichloromethane; methanol / 1 h / 20 °C / Inert atmosphere
4: magnesium bromide diethyl etherate; lithium bromide / dichloromethane / 2.5 h / -15 - -5 °C
5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 20 °C
6: toluene-4-sulfonic acid / methanol; 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere
7: flash chromatography
8: zinc trifluoromethanesulfonate / dichloromethane; nitromethane / 12 h / 20 °C / Inert atmosphere
9: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
10: dichloromethane; n-heptane / 0 - 20 °C / Inert atmosphere
With
N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; magnesium bromide diethyl etherate; zinc trifluoromethanesulfonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; lithium bromide;
In
tetrahydrofuran; methanol; nitromethane; hexane; n-heptane; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/jo302267f