5-O-(tert-butyldimethylsilyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-β-D-ribitol

Base Information

Chemical Name:5-O-(tert-butyldimethylsilyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-β-D-ribitol
CAS No.:180895-70-9
Molecular Formula:C₂₈H₃₈N₂O₅SSi
Molecular Weight:542.772
Hs Code.:

Synonyms:5-O-(tert-butyldimethylsilyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-β-D-ribitol

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Chemical Property of 5-O-(tert-butyldimethylsilyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-β-D-ribitol

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Technology Process of 5-O-(tert-butyldimethylsilyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-β-D-ribitol

There total 4 articles about 5-O-(tert-butyldimethylsilyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-β-D-ribitol 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: 56.0%

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

: 180895-70-9
5-O-(tert-butyldimethylsilyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-β-D-ribitol

Guidance literature:: With 3 A molecular sieve; ammonium formate; sodium cyanoborohydride; In methanol; at 20 ℃; for 18h;
DOI:10.1021/jo960523i

Reference yield:

: 40899-71-6
1-benzenesulfonylindole

: 180895-70-9
5-O-(tert-butyldimethylsilyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-β-D-ribitol

Guidance literature:: Multi-step reaction with 4 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

4.1: 56 percent / ammonium formate; NaBH₃CN; molecular sieves (3A) / methanol / 18 h / 20 °C

With n-butyllithium; 3 A molecular sieve; ammonium formate; sodium cyanoborohydride; dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Metallation / 2.1: Addition / 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Cyclization;
DOI:10.1021/jo960523i

Reference yield:

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

: 180895-70-9
5-O-(tert-butyldimethylsilyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-1-[2-[N-(phenylsulfonyl)indolyl]]-β-D-ribitol

Guidance literature:: Multi-step reaction with 3 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

3.1: 56 percent / ammonium formate; NaBH₃CN; molecular sieves (3A) / methanol / 18 h / 20 °C

With 3 A molecular sieve; ammonium formate; sodium cyanoborohydride; dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; 1.1: Addition / 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Cyclization;
DOI:10.1021/jo960523i