(2S,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate

Base Information

Chemical Name:(2S,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate
CAS No.:1268617-43-1
Molecular Formula:C₁₆H₂₂O₆S
Molecular Weight:342.413
Hs Code.:

Synonyms:(2S,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate

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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,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate

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Technology Process of (2S,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate

There total 6 articles about (2S,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate 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: 62.0%

: 1268617-41-9
(2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-isopropylidenedioxy-4-oxopentanoate

: 1268617-43-1
(2S,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate

Guidance literature:: With diisobutylaluminium hydride; zinc dibromide; In tetrahydrofuran; toluene; at -78 ℃; for 1.5h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201002637

Reference yield:

: 1268617-41-9
(2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-isopropylidenedioxy-4-oxopentanoate

: 1268617-65-7
(2S,3R,4S,SR)-methyl 5-(ptolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate

: 1268617-43-1
(2S,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate

Guidance literature:: With diisobutylaluminium hydride; zinc dibromide; In tetrahydrofuran; toluene; at -78 ℃; for 2h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201002637

Reference yield:

: 1519-39-7
(R)-methyl p-tolyl sulfoxide

: 1268617-43-1
(2S,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; hexane / 1 h / -40 °C

1.2: 3 h / -78 °C

2.1: diisobutylaluminium hydride; zinc dibromide / tetrahydrofuran; toluene / 1.5 h / -78 °C / Inert atmosphere

With n-butyllithium; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; zinc dibromide; In tetrahydrofuran; hexane; toluene;
DOI:10.1002/chem.201002637