(2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-bis(benzyloxy)-4-oxopentanoate

Base Information

Chemical Name:(2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-bis(benzyloxy)-4-oxopentanoate
CAS No.:872167-99-2
Molecular Formula:C₂₇H₂₈O₆S
Molecular Weight:480.582
Hs Code.:

Synonyms:(2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-bis(benzyloxy)-4-oxopentanoate

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Chemical Property of (2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-bis(benzyloxy)-4-oxopentanoate

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Technology Process of (2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-bis(benzyloxy)-4-oxopentanoate

There total 3 articles about (2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-bis(benzyloxy)-4-oxopentanoate 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: 57.0%

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

: 195874-05-6
(2S,3S)-dimethyl 2,3-bis(benzyloxy)succinate

: 872167-99-2
(2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-bis(benzyloxy)-4-oxopentanoate

Guidance literature:: (R)-methyl p-tolyl sulfoxide; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 - -40 ℃;

(2S,3S)-dimethyl 2,3-bis(benzyloxy)succinate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1021/ol0523603

Reference yield:

: 13171-64-7
Dimethyl D-tartrate

: 872167-99-2
(2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-bis(benzyloxy)-4-oxopentanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 12 h / 20 °C

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

2.2: 2 h / -78 °C

With n-butyllithium; trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; cyclohexane;
DOI:10.1002/chem.201002637

Reference yield:

: 100-39-0
benzyl bromide

: 872167-99-2
(2S,3S,SR)-methyl 5-(p-tolylsulfinyl)-2,3-bis(benzyloxy)-4-oxopentanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran

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

2.2: 2 h / -78 °C

With n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane;
DOI:10.1002/chem.201002637