(2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)butan-1-one

Base Information

Chemical Name:(2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)butan-1-one
CAS No.:1373432-37-1
Molecular Formula:C₂₄H₃₉NO₂S₂Si
Molecular Weight:465.797
Hs Code.:

Synonyms:(2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)butan-1-one

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Chemical Property of (2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)butan-1-one

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Technology Process of (2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)butan-1-one

There total 2 articles about (2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)butan-1-one 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: 94.0%

: 1373432-18-8
(2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylbutan-1-one

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 1373432-37-1
(2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)butan-1-one

Guidance literature:: With 2,6-dimethylpyridine; at 0 - 20 ℃; for 0.333333h;
DOI:10.1021/ol300785c

Reference yield:

: 863324-53-2
(R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)propan-1-one

: 1373432-37-1
(2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)butan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

1.2: -78 °C

2.1: 2,6-dimethylpyridine / 0.33 h / 0 - 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ol300785c

Reference yield:

: 1373432-37-1
(2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)butan-1-one

: 1373432-42-8
(2R,3R,5S,6S)-2-allyl-3-(4-methoxybenzyloxy)-5-methyl-6-(triisopropylsilyloxy)heptyl methanesulfonate

Guidance literature:: Multi-step reaction with 8 steps

1.1: methanol; lithium borohydride / tetrahydrofuran; diethyl ether / 0 - 20 °C

2.1: triethylamine / dichloromethane / 0 - 20 °C

3.1: tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 48 h / 60 °C

4.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C

5.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

5.2: 1 h

6.1: methanol; lithium borohydride / tetrahydrofuran; diethyl ether / 0 - 20 °C

7.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h

7.2: 8 h / -78 - 20 °C

8.1: triethylamine / dichloromethane / 0 - 20 °C

With 1-methyl-pyrrolidin-2-one; methanol; lithium borohydride; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol300785c