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

Base Information

Chemical Name:5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3S,4R,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde
CAS No.:1337989-82-8
Molecular Formula:C₄₄H₅₉NO₈Si
Molecular Weight:758.04
Hs Code.:

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

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

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Chemical Property of 5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3S,4R,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde

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Technology Process of 5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3S,4R,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde

There total 9 articles about 5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3S,4R,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-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: 45.0%

: 1337989-73-7
5-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-pyrrole-2-carbaldehyde

: 1337989-81-7
tert-butyldimethyl((2R,3R,4S)-1,3,4-tris(benzyloxy)-4-(oxiran-2-yl)butan-2-yloxy)silane

: 1337989-82-8
5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3S,4R,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde

Guidance literature:: 5-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-pyrrole-2-carbaldehyde; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h; Inert atmosphere;

tert-butyldimethyl((2R,3R,4S)-1,3,4-tris(benzyloxy)-4-(oxiran-2-yl)butan-2-yloxy)silane; In N,N-dimethyl-formamide; at 0 - 55 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1021/ol202121k

Reference yield:

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

: 1337989-82-8
5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3S,4R,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde

Guidance literature:: Multi-step reaction with 2 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

With pyridinium p-toluenesulfonate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol202121k

Reference yield:

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

: 1337989-82-8
5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1-((3S,4R,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 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

With manganese(IV) oxide; sodium tetrahydroborate; pyridinium p-toluenesulfonate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol202121k