(3S,4S,5R,SR)-5-[(p-tolylsulfinyl)methyl]-3,4-bis(benzyloxy)-dihydrofuran-2-one

Base Information

Chemical Name:(3S,4S,5R,SR)-5-[(p-tolylsulfinyl)methyl]-3,4-bis(benzyloxy)-dihydrofuran-2-one
CAS No.:872168-02-0
Molecular Formula:C₂₆H₂₆O₅S
Molecular Weight:450.555
Hs Code.:

Synonyms:(3S,4S,5R,SR)-5-[(p-tolylsulfinyl)methyl]-3,4-bis(benzyloxy)-dihydrofuran-2-one

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Chemical Property of (3S,4S,5R,SR)-5-[(p-tolylsulfinyl)methyl]-3,4-bis(benzyloxy)-dihydrofuran-2-one

Chemical Property:

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Technology Process of (3S,4S,5R,SR)-5-[(p-tolylsulfinyl)methyl]-3,4-bis(benzyloxy)-dihydrofuran-2-one

There total 5 articles about (3S,4S,5R,SR)-5-[(p-tolylsulfinyl)methyl]-3,4-bis(benzyloxy)-dihydrofuran-2-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:

: 872168-01-9
(2S,3R,4R,SR)-methyl 5-(p-tolylsulfinyl)-2,3-bis(benzyloxy)-4-hydroxypentanoate

: 872168-02-0
(3S,4S,5R,SR)-5-[(p-tolylsulfinyl)methyl]-3,4-bis(benzyloxy)-dihydrofuran-2-one

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 50 ℃; for 10h;
DOI:10.1021/ol0523603

Reference yield:

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

: 872168-02-0
(3S,4S,5R,SR)-5-[(p-tolylsulfinyl)methyl]-3,4-bis(benzyloxy)-dihydrofuran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: zinc bromide / tetrahydrofuran / 1 h / 20 °C

1.2: diisobutylaluminum hydride / tetrahydrofuran; toluene / 1.5 h / -78 °C

2.1: 125 mg / trifluoroacetic acid / CH₂Cl₂ / 10 h / 50 °C

With trifluoroacetic acid; zinc dibromide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol0523603

Reference yield:

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

: 872168-02-0
(3S,4S,5R,SR)-5-[(p-tolylsulfinyl)methyl]-3,4-bis(benzyloxy)-dihydrofuran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / -78 - -40 °C

1.2: 57 percent / tetrahydrofuran; hexane / 2 h / -78 °C

2.1: zinc bromide / tetrahydrofuran / 1 h / 20 °C

2.2: diisobutylaluminum hydride / tetrahydrofuran; toluene / 1.5 h / -78 °C

3.1: 125 mg / trifluoroacetic acid / CH₂Cl₂ / 10 h / 50 °C

With trifluoroacetic acid; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0523603