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

Base Information

• Chemical Name: 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
• CAS No.: 1337989-72-6
• Molecular Formula: C₄₄H₅₇NO₈Si
• Molecular Weight: 756.024

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 11 articles about 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 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: 88.0%

5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3S,4S,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde (1337989-78-2) → 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 (1337989-72-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol202121k

Reference yield:

5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde (67350-50-9) → 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 (1337989-72-6)

Guidance literature:

Multi-step reaction with 3 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

With pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol202121k

Reference yield:

(1H-pyrrole-2,5-diyl)dimethanol (6249-04-3) → 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 (1337989-72-6)

Guidance literature:

Multi-step reaction with 5 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

With manganese(IV) oxide; sodium tetrahydroborate; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ol202121k

upstream raw materials:

3,4-dihydro-2H-pyran

(1H-pyrrole-2,5-diyl)dimethanol

2,3,5-tri-O-benzyl-D-ribofuranose

tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-en-2-yloxy)silane

Downstream raw materials:

(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

(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

(3R,4R,5R)-5-(((4-bromobenzoyl)oxy)methyl)-6'-formyl-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-3,4-diyl bis(4-bromobenzoate)

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