(3R,4R,5S)-[5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl]carbamic acid benzyl ester

Base Information

Chemical Name:(3R,4R,5S)-[5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl]carbamic acid benzyl ester
CAS No.:852063-49-1
Molecular Formula:C₂₇H₃₄N₂O₅Si
Molecular Weight:494.663
Hs Code.:

Synonyms:(3R,4R,5S)-[5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl]carbamic acid benzyl ester

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Chemical Property of (3R,4R,5S)-[5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl]carbamic acid benzyl ester

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Technology Process of (3R,4R,5S)-[5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl]carbamic acid benzyl ester

There total 4 articles about (3R,4R,5S)-[5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl]carbamic acid benzyl ester 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: 63.0%

: 852063-48-0
(3S,4S,5S)-5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-carboxylic acid

: 100-51-6,185532-71-2
benzyl alcohol

: 852063-49-1
(3R,4R,5S)-[5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl]carbamic acid benzyl ester

Guidance literature:: (3S,4S,5S)-5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-carboxylic acid; With diphenyl-phosphinic acid; triethylamine; In acetonitrile; for 3h;

In toluene; at 70 ℃; for 1h;

benzyl alcohol; In toluene; at 70 ℃; for 20h;
DOI:10.1016/j.tetasy.2005.02.008

Reference yield:

: 120-72-9
indole

: 852063-49-1
(3R,4R,5S)-[5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 76 percent / DL-proline / acetonitrile / 36 h / 20 °C

2.1: 92 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C

3.1: 90 percent / imidazole / CH₂Cl₂; dimethylformamide / 20 h / 20 °C

4.1: Et₃N; DPPA / acetonitrile / 3 h

4.2: toluene / 1 h / 70 °C

4.3: 63 percent / toluene / 20 h / 70 °C

With 1H-imidazole; hydrogenchloride; diphenyl-phosphinic acid; triethylamine; rac-Pro-OH; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4.1: Curtius rearrangement;
DOI:10.1016/j.tetasy.2005.02.008

Reference yield:

: 325481-23-0
(3S,4S,5S)-5-hydroxymethyl-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-carboxylic acid

: 852063-49-1
(3R,4R,5S)-[5-(tert-butyldimethylsilanyloxymethyl)-4-(1H-indol-3-yl)-2-oxotetrahydrofuran-3-yl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / imidazole / CH₂Cl₂; dimethylformamide / 20 h / 20 °C

2.1: Et₃N; DPPA / acetonitrile / 3 h

2.2: toluene / 1 h / 70 °C

2.3: 63 percent / toluene / 20 h / 70 °C

With 1H-imidazole; diphenyl-phosphinic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Curtius rearrangement;
DOI:10.1016/j.tetasy.2005.02.008