(2S)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]-2-(p-toluenesulfonyloxy)tetrahydrofuran

Base Information

Chemical Name:(2S)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]-2-(p-toluenesulfonyloxy)tetrahydrofuran
CAS No.:254891-82-2
Molecular Formula:C₂₄H₂₈O₆S
Molecular Weight:444.549
Hs Code.:

Synonyms:(2S)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]-2-(p-toluenesulfonyloxy)tetrahydrofuran

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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 (2S)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]-2-(p-toluenesulfonyloxy)tetrahydrofuran

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Technology Process of (2S)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]-2-(p-toluenesulfonyloxy)tetrahydrofuran

There total 9 articles about (2S)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]-2-(p-toluenesulfonyloxy)tetrahydrofuran 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: 78.0%

: 98-59-9
p-toluenesulfonyl chloride

: 253867-31-1
(2S)-2-(hydroxymethyl)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]tetrahydrofuran

: 254891-82-2
(2S)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]-2-(p-toluenesulfonyloxy)tetrahydrofuran

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 8h;
DOI:10.1016/j.tetasy.2005.01.045

Reference yield:

: 36326-38-2,64520-58-7,91057-97-5,91926-90-8,104321-62-2,124818-64-0,128525-67-7,128525-69-9,104321-63-3,917877-01-1
ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate

: 254891-82-2
(2S)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]-2-(p-toluenesulfonyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / H₂ / PtO₂ / ethyl acetate / 4 h / 20 °C

2.1: 97 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 - 20 °C

3.1: IBX / dimethylsulfoxide / 4 h / 0 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 55 percent / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

6.1: 89 percent / acetic acid / H₂O / 12 h / 20 °C

7.1: 77 percent / Et₃N / CH₂Cl₂ / 10 h / 20 °C

8.1: 93 percent / K₂CO₃ / methanol / 3 h / 20 °C

9.1: 78 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; hydrogen; potassium carbonate; acetic acid; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;
DOI:10.1016/j.tetasy.2005.01.045

Reference yield:

: 133008-09-0
(R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propanal

: 254891-82-2
(2S)-5-[1-(4-methoxybenzyloxy)-3-butyn-4-yl]-2-(p-toluenesulfonyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 55 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

3.1: 89 percent / acetic acid / H₂O / 12 h / 20 °C

4.1: 77 percent / Et₃N / CH₂Cl₂ / 10 h / 20 °C

5.1: 93 percent / K₂CO₃ / methanol / 3 h / 20 °C

6.1: 78 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

With dmap; n-butyllithium; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1016/j.tetasy.2005.01.045