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

Base Information

• Chemical Name: 5-((tert-butyldimethylsilyloxy)methyl)-1-((3S,4S,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde
• CAS No.: 1337989-94-2
• Molecular Formula: C₄₅H₆₅NO₇Si₂
• Molecular Weight: 788.185

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

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

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

There total 9 articles about 5-((tert-butyldimethylsilyloxy)methyl)-1-((3S,4S,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: 14.0%

5-((tert-butyldimethylsilyloxy)methyl)-1H-pyrrole-2-carbaldehyde (1337989-91-9) + tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)-4-(oxiran-2-yl)butan-2-yloxy)silane (1337989-75-9) → 5-((tert-butyldimethylsilyloxy)methyl)-1-((3S,4S,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde (1337989-94-2)

Guidance literature:

5-((tert-butyldimethylsilyloxy)methyl)-1H-pyrrole-2-carbaldehyde; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)-4-(oxiran-2-yl)butan-2-yloxy)silane; In tetrahydrofuran; at 0 ℃; regioselective reaction; Inert atmosphere; Reflux;

DOI:10.1021/ol202121k

Reference yield:

5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde (67350-50-9) → 5-((tert-butyldimethylsilyloxy)methyl)-1-((3S,4S,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde (1337989-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere; Reflux

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol202121k

Reference yield:

(1H-pyrrole-2,5-diyl)dimethanol (6249-04-3) → 5-((tert-butyldimethylsilyloxy)methyl)-1-((3S,4S,5R)-3,4,6-tris(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2-hydroxyhexyl)-1H-pyrrole-2-carbaldehyde (1337989-94-2)

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: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

4.2: 0 °C / Inert atmosphere; Reflux

With manganese(IV) oxide; sodium tetrahydroborate; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1021/ol202121k

upstream raw materials:

(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

5-((tert-butyldimethylsilyloxy)methyl)-1H-pyrrole-2-carbaldehyde

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