(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

Base Information

Chemical Name:(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
CAS No.:1337989-80-6
Molecular Formula:C₃₃H₃₃NO₆
Molecular Weight:539.628
Hs Code.:

Synonyms:(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

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Chemical Property of (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

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Technology Process of (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

There total 10 articles about (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-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:

Reference yield: 30.0%

: 1337989-72-6
5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3R,4S,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-oxohexyl)-1H-pyrrole-2-carbaldehyde

: 1337989-96-4
(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

: 1337989-80-6
(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 0 - 20 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol202121k

Reference yield:

: 67350-50-9
5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde

: 1337989-80-6
(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

Guidance literature:: 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

Reference yield:

: 6249-04-3
(1H-pyrrole-2,5-diyl)dimethanol

: 1337989-80-6
(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde

Guidance literature:: 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