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

Base Information

Chemical Name:(2R,3R,5S,6S)-2-allyl-3-(4-methoxybenzyloxy)-5-methyl-6-(triisopropylsilyloxy)heptyl methanesulfonate
CAS No.:1373432-42-8
Molecular Formula:C₂₉H₅₂O₆SSi
Molecular Weight:556.88
Hs Code.:

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

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Chemical Property of (2R,3R,5S,6S)-2-allyl-3-(4-methoxybenzyloxy)-5-methyl-6-(triisopropylsilyloxy)heptyl methanesulfonate

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Technology Process of (2R,3R,5S,6S)-2-allyl-3-(4-methoxybenzyloxy)-5-methyl-6-(triisopropylsilyloxy)heptyl methanesulfonate

There total 9 articles about (2R,3R,5S,6S)-2-allyl-3-(4-methoxybenzyloxy)-5-methyl-6-(triisopropylsilyloxy)heptyl methanesulfonate 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: 97.0%

: 1373432-24-6
(2R,3R,5S,6S)-2-allyl-3-(4-methoxybenzyloxy)-5-methyl-6-(triisopropylsilyloxy)heptan-1-ol

: 124-63-0
methanesulfonyl chloride

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

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol300785c

Reference yield:

: 1373432-39-3
(2S,3S)-2-methyl-3-(triisopropylsilyloxy)butan-1-ol

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

Guidance literature:: Multi-step reaction with 7 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C

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

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

4.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

4.2: 1 h

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

6.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h

6.2: 8 h / -78 - 20 °C

7.1: 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

Reference yield:

: 1373432-20-2
(2S,3S)-2-methyl-3-(triisopropylsilyloxy)butyl methanesulfonate

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

Guidance literature:: Multi-step reaction with 6 steps

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

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

3.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

3.2: 1 h

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

5.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h

5.2: 8 h / -78 - 20 °C

6.1: 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