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

Base Information

Chemical Name:(2S,3R,4R,SR)-4-hydroxy-2,3-isopropylidenedioxy-N-methoxy-N-methyl-5-(p-tolylsulfinyl)
CAS No.:1268617-44-2
Molecular Formula:C₁₇H₂₅NO₆S
Molecular Weight:371.455
Hs Code.:

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

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Chemical Property of (2S,3R,4R,SR)-4-hydroxy-2,3-isopropylidenedioxy-N-methoxy-N-methyl-5-(p-tolylsulfinyl)

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

There total 4 articles about (2S,3R,4R,SR)-4-hydroxy-2,3-isopropylidenedioxy-N-methoxy-N-methyl-5-(p-tolylsulfinyl) 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: 80.0%

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

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 1268617-44-2
(2S,3R,4R,SR)-4-hydroxy-2,3-isopropylidenedioxy-N-methoxy-N-methyl-5-(p-tolylsulfinyl)

Guidance literature:: N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In dichloromethane; toluene; at 0 ℃; for 0.5h;

(2S,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-4-hydroxy-2,3-isopropylidenedioxy pentanoate; In dichloromethane; toluene; at 20 ℃;
DOI:10.1002/chem.201002637

Reference yield:

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

: 1268617-44-2
(2S,3R,4R,SR)-4-hydroxy-2,3-isopropylidenedioxy-N-methoxy-N-methyl-5-(p-tolylsulfinyl)

Guidance literature:: Multi-step reaction with 3 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

3.1: trimethylaluminum / dichloromethane; toluene / 0.5 h / 0 °C

3.2: 20 °C

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

Reference yield:

: 37031-29-1,6134-82-3,6135-80-4,90613-41-5,116499-08-2,37031-30-4
(+)-dimethyl-2,3-O-isopropylidene-D-tartrate

: 1268617-44-2
(2S,3R,4R,SR)-4-hydroxy-2,3-isopropylidenedioxy-N-methoxy-N-methyl-5-(p-tolylsulfinyl)

Guidance literature:: Multi-step reaction with 3 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

3.1: trimethylaluminum / dichloromethane; toluene / 0.5 h / 0 °C

3.2: 20 °C

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