(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

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-pent-4-ynoic acid dimethylamide
CAS No.:634911-89-0
Molecular Formula:C₄₃H₅₄N₂O₈Si
Molecular Weight:754.996
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-pent-4-ynoic 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-pent-4-ynoic 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-pent-4-ynoic 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-pent-4-ynoic acid dimethylamide

There total 9 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-pent-4-ynoic 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: 91.7%

: 545362-97-8
acetic acid 2-(2-iodo-6,7-dimethoxy-1H-indole030yl)-ethyl ester

: 634911-88-9
(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pent-4-ynoic acid dimethylamide

: 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

Guidance literature:: With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; at 65 ℃; for 1h;
DOI:10.1016/j.tet.2003.09.005

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 9 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

With dmap; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 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

: 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

Guidance literature:: Multi-step reaction with 8 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

With dmap; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 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