Technology Process of (2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
There total 10 articles about (2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde 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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1337990-05-2
(2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
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1337989-84-0
(2S,3R,4S,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
- Guidance literature:
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With
toluene-4-sulfonic acid;
In
dichloromethane;
at 0 - 20 ℃;
optical yield given as %de;
Inert atmosphere;
DOI:10.1021/ol202121k
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1337990-05-2
(2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
- Guidance literature:
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Multi-step reaction with 4 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 20 h / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere
2.2: 0 - 55 °C / Inert atmosphere
3.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
4.1: toluene-4-sulfonic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
With
pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid;
In
dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol202121k
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1337990-05-2
(2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: manganese(IV) oxide / acetone / 20 °C / Inert atmosphere
2.1: sodium tetrahydroborate / methanol / 0.25 h / 0 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / dichloromethane / 20 h / Inert atmosphere
4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere
4.2: 0 - 55 °C / Inert atmosphere
5.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
6.1: toluene-4-sulfonic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
With
manganese(IV) oxide; sodium tetrahydroborate; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid;
In
methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol202121k