(2S)-5-acetoxy-2-hydroxy-9-(4-methoxybenzyloxy)-1-(p-toluenesulfonyloxy)non-6-yne

Base Information

Chemical Name:(2S)-5-acetoxy-2-hydroxy-9-(4-methoxybenzyloxy)-1-(p-toluenesulfonyloxy)non-6-yne
CAS No.:254891-81-1
Molecular Formula:C₂₆H₃₂O₈S
Molecular Weight:504.601
Hs Code.:

Synonyms:(2S)-5-acetoxy-2-hydroxy-9-(4-methoxybenzyloxy)-1-(p-toluenesulfonyloxy)non-6-yne

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Chemical Property of (2S)-5-acetoxy-2-hydroxy-9-(4-methoxybenzyloxy)-1-(p-toluenesulfonyloxy)non-6-yne

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Technology Process of (2S)-5-acetoxy-2-hydroxy-9-(4-methoxybenzyloxy)-1-(p-toluenesulfonyloxy)non-6-yne

There total 7 articles about (2S)-5-acetoxy-2-hydroxy-9-(4-methoxybenzyloxy)-1-(p-toluenesulfonyloxy)non-6-yne 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: 81.0%

: 98-59-9
p-toluenesulfonyl chloride

: 851532-55-3
(2R)-5-acetoxy-1,2-dihydroxy-9-(4-methoxybenzyloxy)non-6-yne

: 254891-81-1
(2S)-5-acetoxy-2-hydroxy-9-(4-methoxybenzyloxy)-1-(p-toluenesulfonyloxy)non-6-yne

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 10h;
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

: 254891-81-1
(2S)-5-acetoxy-2-hydroxy-9-(4-methoxybenzyloxy)-1-(p-toluenesulfonyloxy)non-6-yne

Guidance literature:: Multi-step reaction with 7 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: 81 percent / Et₃N / CH₂Cl₂ / 10 h / 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; hydrogen; acetic acid; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; platinum(IV) oxide; In tetrahydrofuran; 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

: 254891-81-1
(2S)-5-acetoxy-2-hydroxy-9-(4-methoxybenzyloxy)-1-(p-toluenesulfonyloxy)non-6-yne

Guidance literature:: Multi-step reaction with 4 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: 81 percent / Et₃N / CH₂Cl₂ / 10 h / 20 °C

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