Technology Process of (2R,4aR,5aS,7aR,8aS,12aR,13aS,14aR,15aS)-2-(((2S,3R,4aS,5aR,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexahydropyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin-3(2H)-one
There total 10 articles about (2R,4aR,5aS,7aR,8aS,12aR,13aS,14aR,15aS)-2-(((2S,3R,4aS,5aR,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexahydropyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin-3(2H)-one 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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1415891-41-6
(2R,4aR,5aS,7aR,8aS,12aR,13aS,14aR,15aS)-2-(((2S,3R,4aS,5aR,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexahydropyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin-3(2H)-one
- Guidance literature:
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With
1,8-diazabicyclo[5.4.0]undec-7-ene;
In
dichloromethane;
at 20 ℃;
for 0.5h;
DOI:10.1021/jo302267f
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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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1415891-41-6
(2R,4aR,5aS,7aR,8aS,12aR,13aS,14aR,15aS)-2-(((2S,3R,4aS,5aR,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexahydropyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin-3(2H)-one
- Guidance literature:
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Multi-step reaction with 8 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
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; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate;
DOI:10.1021/jo302267f
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1415891-41-6
(2R,4aR,5aS,7aR,8aS,12aR,13aS,14aR,15aS)-2-(((2S,3R,4aS,5aR,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexahydropyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin-3(2H)-one
- Guidance literature:
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Multi-step reaction with 9 steps
1: toluene-4-sulfonic acid / chloroform / 7 h / 55 °C / Inert atmosphere
2: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
3: hydrogen; 10 wt% Pd(OH)2 on carbon / ethyl acetate / 18 h / 20 °C
4: 2,6-dimethylpyridine / tetrahydrofuran / 0.5 h / -80 °C / Inert atmosphere
5: tetrahydrofuran / 0.67 h / -80 °C / Inert atmosphere
6: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; hexane / -100 °C / Inert atmosphere
7: toluene-4-sulfonic acid / dichloromethane; methanol / 1 h / 20 °C / Inert atmosphere
8: magnesium bromide diethyl etherate; lithium bromide / dichloromethane / 2.5 h / -15 - -5 °C
9: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 20 °C
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; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; ethyl acetate;
DOI:10.1021/jo302267f