1,3-O-benzylidene-2-O-(but-2'-ynyl)-4-O-t-butyldimethylsilyl-D-threitol

Base Information

Chemical Name:1,3-O-benzylidene-2-O-(but-2'-ynyl)-4-O-t-butyldimethylsilyl-D-threitol
CAS No.:848771-16-4
Molecular Formula:C₂₁H₃₂O₄Si
Molecular Weight:376.568
Hs Code.:

Synonyms:1,3-O-benzylidene-2-O-(but-2'-ynyl)-4-O-t-butyldimethylsilyl-D-threitol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 1,3-O-benzylidene-2-O-(but-2'-ynyl)-4-O-t-butyldimethylsilyl-D-threitol

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Technology Process of 1,3-O-benzylidene-2-O-(but-2'-ynyl)-4-O-t-butyldimethylsilyl-D-threitol

There total 5 articles about 1,3-O-benzylidene-2-O-(but-2'-ynyl)-4-O-t-butyldimethylsilyl-D-threitol 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: 98.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1027307-97-6
1,3-O-benzylidene-2-O-(but-2'-ynyl)-D-threitol

: 848771-16-4
1,3-O-benzylidene-2-O-(but-2'-ynyl)-4-O-t-butyldimethylsilyl-D-threitol

Guidance literature:: With 1H-imidazole; In acetonitrile; at 0 - 20 ℃; for 2h;
DOI:10.1002/ejoc.200400557

Reference yield:

: 81577-58-4
1,3-(R)-O-benzylidene-D-threitol

: 848771-16-4
1,3-O-benzylidene-2-O-(but-2'-ynyl)-4-O-t-butyldimethylsilyl-D-threitol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / DMAP / pyridine / 12 h / 70 °C

2.1: 80 percent / KOH; Bu₄NBr / toluene / 24 h / 20 °C

3.1: nBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; heptane / 0.67 h / -45 °C

3.2: 90 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; heptane / 1 h / -45 - 20 °C

4.1: 76 percent / p-TsOH / methanol / 0.5 h / 20 °C

5.1: 98 percent / imidazole / acetonitrile / 2 h / 0 - 20 °C

With 1H-imidazole; dmap; potassium hydroxide; n-butyllithium; tetrabutylammomium bromide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; n-heptane; toluene; acetonitrile;
DOI:10.1002/ejoc.200400557

Reference yield:

: 1,3-O-benzylidene-4-O-trityl-D-threitol

: 848771-16-4
1,3-O-benzylidene-2-O-(but-2'-ynyl)-4-O-t-butyldimethylsilyl-D-threitol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 80 percent / KOH; Bu₄NBr / toluene / 24 h / 20 °C

2.1: nBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; heptane / 0.67 h / -45 °C

2.2: 90 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; heptane / 1 h / -45 - 20 °C

3.1: 76 percent / p-TsOH / methanol / 0.5 h / 20 °C

4.1: 98 percent / imidazole / acetonitrile / 2 h / 0 - 20 °C

With 1H-imidazole; potassium hydroxide; n-butyllithium; tetrabutylammomium bromide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; n-heptane; toluene; acetonitrile;
DOI:10.1002/ejoc.200400557