2-(trimethylsilyl)ethyl N-(2-indol-3'-ylethyl)-N-<(4(R),5(R)-dihydroxy-3(R)-((methanesulfonyl)oxy)cyclohex-1(S)-yl)methyl>carbamate

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Chemical Name:2-(trimethylsilyl)ethyl N-(2-indol-3'-ylethyl)-N-<(4(R),5(R)-dihydroxy-3(R)-((methanesulfonyl)oxy)cyclohex-1(S)-yl)methyl>carbamate
CAS No.:101917-59-3
Molecular Formula:C₂₄H₃₈N₂O₇SSi
Molecular Weight:526.726
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl N-(2-indol-3'-ylethyl)-N-<(4(R),5(R)-dihydroxy-3(R)-((methanesulfonyl)oxy)cyclohex-1(S)-yl)methyl>carbamate

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Chemical Property of 2-(trimethylsilyl)ethyl N-(2-indol-3'-ylethyl)-N-<(4(R),5(R)-dihydroxy-3(R)-((methanesulfonyl)oxy)cyclohex-1(S)-yl)methyl>carbamate

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Technology Process of 2-(trimethylsilyl)ethyl N-(2-indol-3'-ylethyl)-N-<(4(R),5(R)-dihydroxy-3(R)-((methanesulfonyl)oxy)cyclohex-1(S)-yl)methyl>carbamate

There total 15 articles about 2-(trimethylsilyl)ethyl N-(2-indol-3'-ylethyl)-N-<(4(R),5(R)-dihydroxy-3(R)-((methanesulfonyl)oxy)cyclohex-1(S)-yl)methyl>carbamate 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: 98.0%

: 101917-58-2
2-(trimethylsilyl)ethyl N-(2-indol-3'-ylethyl)-N-<(4,5-O-isopropylidene-4(R),5(R)-dihydroxy-3(R)-((methanesulfonyl)oxy)cyclohex-1(S)-yl)methyl>carbamate

: 101917-59-3
2-(trimethylsilyl)ethyl N-(2-indol-3'-ylethyl)-N-<(4(R),5(R)-dihydroxy-3(R)-((methanesulfonyl)oxy)cyclohex-1(S)-yl)methyl>carbamate

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; water; at 25 ℃; for 16h;
DOI:10.1021/jo00362a030

Reference yield:

: 32384-42-2
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

: 101917-59-3
2-(trimethylsilyl)ethyl N-(2-indol-3'-ylethyl)-N-<(4(R),5(R)-dihydroxy-3(R)-((methanesulfonyl)oxy)cyclohex-1(S)-yl)methyl>carbamate

Guidance literature:: Multi-step reaction with 13 steps

1: 87 percent / lithium aluminum hydride / tetrahydrofuran / 18 h / Heating

2: 80 percent / benzoic acid, triethyl orthoformate / 130 - 200 °C

3: 92 percent / triethylamine, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 2 h / 0 °C

5: 91 percent / sodium azide / dimethylformamide / 12 h / 50 °C

6: 77 percent / imidazole / dimethylformamide / 14 h / 25 °C

7: 97 percent / hydrogen / 10percent palladium on carbon / tetrahydrofuran / 5 h

8: 1.) triethylamine, diphenylphosphoryl azide / 1.) DMF, -20 deg C, 30 min, 2.) a) -20 deg C, 3 h, b) 25 deg C, 12 h

9: 95 percent / diisobutylaluminum hydride (DIBAL-H) / tetrahydrofuran; toluene / 4 h / Heating

10: 90 percent / triethylamine / CH₂Cl₂ / 3 h / 0 °C

11: 82 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C

12: 91 percent / triethylamine / CH₂Cl₂ / 3 h / 0 °C

13: 98 percent / HCl / tetrahydrofuran; H₂O / 16 h / 25 °C

With 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; sodium azide; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; triethylamine; orthoformic acid triethyl ester; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00362a030

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 101917-59-3
2-(trimethylsilyl)ethyl N-(2-indol-3'-ylethyl)-N-<(4(R),5(R)-dihydroxy-3(R)-((methanesulfonyl)oxy)cyclohex-1(S)-yl)methyl>carbamate

Guidance literature:: Multi-step reaction with 14 steps

1: 78 percent / dry HCl / 24 h / 25 °C

2: 87 percent / lithium aluminum hydride / tetrahydrofuran / 18 h / Heating

3: 80 percent / benzoic acid, triethyl orthoformate / 130 - 200 °C

4: 92 percent / triethylamine, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 2 h / 0 °C

6: 91 percent / sodium azide / dimethylformamide / 12 h / 50 °C

7: 77 percent / imidazole / dimethylformamide / 14 h / 25 °C

8: 97 percent / hydrogen / 10percent palladium on carbon / tetrahydrofuran / 5 h

9: 1.) triethylamine, diphenylphosphoryl azide / 1.) DMF, -20 deg C, 30 min, 2.) a) -20 deg C, 3 h, b) 25 deg C, 12 h

10: 95 percent / diisobutylaluminum hydride (DIBAL-H) / tetrahydrofuran; toluene / 4 h / Heating

11: 90 percent / triethylamine / CH₂Cl₂ / 3 h / 0 °C

12: 82 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C

13: 91 percent / triethylamine / CH₂Cl₂ / 3 h / 0 °C

14: 98 percent / HCl / tetrahydrofuran; H₂O / 16 h / 25 °C

With 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; sodium azide; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; triethylamine; orthoformic acid triethyl ester; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00362a030