Technology Process of 5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy2,5-(pent-4-enimido)-L-gulohexonamide
There total 12 articles about 5-(adamantan-1-yl-methoxy)pentyl 3,4,6-tri-O-benzyl-2,5-dideoxy2,5-(pent-4-enimido)-L-gulohexonamide which
guide to synthetic route it.
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synthetic route:
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16838-89-4,17073-88-0,60933-68-8,60933-69-9,73068-66-3,89361-52-4,89615-42-9,89615-45-2,96192-07-3
2,3,5-tri-O-benzyl-D-xylofuranose
- Guidance literature:
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Multi-step reaction with 8 steps
1: sodium tetrahydroborate / methanol / 3 h / 20 °C / Inert atmosphere
2: pyridine / 20 h / 40 °C / Inert atmosphere
3: triethylamine / dichloromethane / 20 h
4: sodium azide; 15-crown-5 / N,N-dimethyl-formamide / 48 h / 90 °C / Inert atmosphere
5: methanol; boron trifluoride diethyl etherate / toluene / 3 h / Inert atmosphere
6: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
7: trimethylphosphane / methanol; toluene / 3 h / 0 °C / Inert atmosphere
8: methanol / 0 - 5 °C / Inert atmosphere
With
pyridine; methanol; sodium tetrahydroborate; sodium azide; 15-crown-5; boron trifluoride diethyl etherate; Dess-Martin periodane; triethylamine; trimethylphosphane;
In
methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
8: |Ugi Condensation;
DOI:10.1002/ejoc.201200923
- Guidance literature:
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Multi-step reaction with 5 steps
1: sodium azide / dimethyl sulfoxide / 20 h / 20 °C / Inert atmosphere
2: water; trimethylphosphane / tetrahydrofuran / 3 h / 0 °C
3: dichloromethane / 20 h / 0 - 20 °C
4: triethylamine; trichlorophosphate / dichloromethane / 1 h / -30 °C / Inert atmosphere
5: methanol / 0 - 5 °C / Inert atmosphere
With
methanol; sodium azide; water; triethylamine; trichlorophosphate; trimethylphosphane;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
5: |Ugi Condensation;
DOI:10.1002/ejoc.201200923
- Guidance literature:
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Multi-step reaction with 3 steps
1: dichloromethane / 20 h / 0 - 20 °C
2: triethylamine; trichlorophosphate / dichloromethane / 1 h / -30 °C / Inert atmosphere
3: methanol / 0 - 5 °C / Inert atmosphere
With
methanol; triethylamine; trichlorophosphate;
In
dichloromethane;
3: |Ugi Condensation;
DOI:10.1002/ejoc.201200923