Technology Process of (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,20aS,21aR,22aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-octacosahydropyrano[3,2-b]pyrano[2,3-j:6,5-j']bis(pyrano[2',3':5,6]pyrano[3,2-b]oxepine)
There total 12 articles about (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,20aS,21aR,22aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-octacosahydropyrano[3,2-b]pyrano[2,3-j:6,5-j']bis(pyrano[2',3':5,6]pyrano[3,2-b]oxepine) 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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1415891-67-6
(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,20aS,21aR,22aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-20a-methoxyoctacosahydropyrano[3,2-b]pyrano[2,3-j:6,5-j']bis(pyrano[2',3':5,6]pyrano[3,2-b]oxepine)
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1415891-47-2
(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,20aS,21aR,22aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-octacosahydropyrano[3,2-b]pyrano[2,3-j:6,5-j']bis(pyrano[2',3':5,6]pyrano[3,2-b]oxepine)
- Guidance literature:
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With
triethylsilane; trimethylsilyl trifluoromethanesulfonate;
In
dichloromethane;
at 0 ℃;
for 1h;
Inert atmosphere;
DOI:10.1021/jo302267f
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1415891-47-2
(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,20aS,21aR,22aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-octacosahydropyrano[3,2-b]pyrano[2,3-j:6,5-j']bis(pyrano[2',3':5,6]pyrano[3,2-b]oxepine)
- Guidance literature:
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Multi-step reaction with 14 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
10: boron trifluoride diethyl etherate / hexane; dichloromethane / 3 h / -80 °C / Inert atmosphere; Molecular sieve
11: pyridinium p-toluenesulfonate / dichloromethane; methanol / 3.5 h / 20 °C / Inert atmosphere
12: toluene-4-sulfonic acid / methanol; 1,2-dichloro-ethane / 17 h / 80 °C / Inert atmosphere
13: methanol; 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
14: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 1 h / 0 °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; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; 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; 1,2-dichloro-ethane;
DOI:10.1021/jo302267f
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1415891-31-4
(2R,3S,4aR,5aS,6aR,10aS,11aR,13aS)-3-(benzyloxy)-2-((benzyloxy)methyl)tetradecahydro-2H-pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepine
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1415891-47-2
(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,20aS,21aR,22aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-octacosahydropyrano[3,2-b]pyrano[2,3-j:6,5-j']bis(pyrano[2',3':5,6]pyrano[3,2-b]oxepine)
- Guidance literature:
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Multi-step reaction with 12 steps
1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethyl acetate / 18 h / 20 °C
2: 2,6-dimethylpyridine / tetrahydrofuran / 0.5 h / -80 °C / Inert atmosphere
3: tetrahydrofuran / 0.67 h / -80 °C / Inert atmosphere
4: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; hexane / -100 °C / Inert atmosphere
5: toluene-4-sulfonic acid / dichloromethane; methanol / 1 h / 20 °C / Inert atmosphere
6: magnesium bromide diethyl etherate; lithium bromide / dichloromethane / 2.5 h / -15 - -5 °C
7: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 20 °C
8: boron trifluoride diethyl etherate / hexane; dichloromethane / 3 h / -80 °C / Inert atmosphere; Molecular sieve
9: pyridinium p-toluenesulfonate / dichloromethane; methanol / 3.5 h / 20 °C / Inert atmosphere
10: toluene-4-sulfonic acid / methanol; 1,2-dichloro-ethane / 17 h / 80 °C / Inert atmosphere
11: methanol; 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
12: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 1 h / 0 °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; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; 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; 1,2-dichloro-ethane;
DOI:10.1021/jo302267f