(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide

Base Information

Chemical Name:(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide
CAS No.:634912-20-2
Molecular Formula:C₄₃H₅₈N₂O₈Si
Molecular Weight:759.028
Hs Code.:

(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide

Synonyms:(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide

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Chemical Property of (3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide

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Technology Process of (3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide

There total 14 articles about (3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide 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:

: 634911-89-0
(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pent-4-ynoic acid dimethylamide

: 634912-20-2
(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol; water; at 20 ℃; for 5.5h;
DOI:10.1016/j.tet.2003.09.005

Reference yield:

: 634911-85-6
(2S)-3-[(trimethyl-silanyl)-ethynyl]-cyclopent-2-enol

: 634912-20-2
(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide

Guidance literature:: Multi-step reaction with 10 steps

1: 84 percent / xylene / 2 h / Heating

2: N-methylmorpholine N-oxide; osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol / 1.5 h / 0 - 20 °C

3: sodium periodate / tetrahydrofuran; H₂O / 1 h / 0 °C

4: 5.47 g / sodium borohydride / ethanol / 0.33 h / 20 °C

5: 75.3 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.5 h / -5 °C

6: 94.6 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 0.75 h / -65 - 5 °C

7: p-toluenesulfonic acid monohydrate / benzene / 2.5 h / Heating

8: 5.14 g / potassium carbonate / methanol / 2 h / 50 °C

9: 91.7 percent / triethylamine; copper(I) iodide; tetrakis(triphenylphosphine)palladium⁽⁰⁾ / 1 h / 65 °C

10: hydrogen / palladium on carbon / ethanol; H₂O / 5.5 h / 20 °C

With dmap; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; xylene; tert-butyl alcohol; benzene; 1: Claisen-Eschenmoser rearrangement / 6: Swern oxidation / 9: Sonogashira coupling;
DOI:10.1016/j.tet.2003.09.005

Reference yield:

: 634911-86-7
(2R)-N,N-dimethyl-2-[1-[(trimethyl-silanyl)-ethynyl]-cyclopent-2-enyl]-acetamide

: 634912-20-2
(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide

Guidance literature:: Multi-step reaction with 9 steps

1: N-methylmorpholine N-oxide; osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol / 1.5 h / 0 - 20 °C

2: sodium periodate / tetrahydrofuran; H₂O / 1 h / 0 °C

3: 5.47 g / sodium borohydride / ethanol / 0.33 h / 20 °C

4: 75.3 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.5 h / -5 °C

5: 94.6 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 0.75 h / -65 - 5 °C

6: p-toluenesulfonic acid monohydrate / benzene / 2.5 h / Heating

7: 5.14 g / potassium carbonate / methanol / 2 h / 50 °C

8: 91.7 percent / triethylamine; copper(I) iodide; tetrakis(triphenylphosphine)palladium⁽⁰⁾ / 1 h / 65 °C

9: hydrogen / palladium on carbon / ethanol; H₂O / 5.5 h / 20 °C

With dmap; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; tert-butyl alcohol; benzene; 5: Swern oxidation / 8: Sonogashira coupling;
DOI:10.1016/j.tet.2003.09.005