(2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-1,4-pentanedione

Base Information

Chemical Name:(2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-1,4-pentanedione
CAS No.:180895-67-4
Molecular Formula:C₂₈H₃₅NO₇SSi
Molecular Weight:557.74
Hs Code.:

Synonyms:(2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-1,4-pentanedione

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Chemical Property of (2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-1,4-pentanedione

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Technology Process of (2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-1,4-pentanedione

There total 3 articles about (2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-1,4-pentanedione 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: 86.0%

: 196106-56-6
5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-D-ribitol

: 180895-67-4
(2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-1,4-pentanedione

Guidance literature:: 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-D-ribitol; With dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; at -78 ℃; for 2h;

With triethylamine; In dichloromethane; at -78 - 0 ℃; for 0.5h;
DOI:10.1021/jo960523i

Reference yield:

: 40899-71-6
1-benzenesulfonylindole

: 180895-67-4
(2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-1,4-pentanedione

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C

2.1: 71 percent / tetrahydrofuran / 1 h / 0 - 20 °C

3.1: DMSO; trifluoroacetic anhydride / CH₂Cl₂ / 2 h / -78 °C

3.2: 86 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

With n-butyllithium; dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; hexane; dichloromethane; 1.1: Metallation / 2.1: Addition / 3.1: Swern oxidation / 3.2: Swern oxidation;
DOI:10.1021/jo960523i

Reference yield:

: 40900-03-6
1-(benzenesulfonyl)-2-lithioindole

: 180895-67-4
(2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-1,4-pentanedione

Guidance literature:: Multi-step reaction with 2 steps

1.1: 71 percent / tetrahydrofuran / 1 h / 0 - 20 °C

2.1: DMSO; trifluoroacetic anhydride / CH₂Cl₂ / 2 h / -78 °C

2.2: 86 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

With dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; 1.1: Addition / 2.1: Swern oxidation / 2.2: Swern oxidation;
DOI:10.1021/jo960523i