(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyl-diphenyl-silanyloxy)-3'-dimethylcarbamoylmethyl-3'-[1,3]dioxolan-2''-yl-hexyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyl-diphenyl-silanyloxy)-3'-dimethylcarbamoylmethyl-3'-[1,3]dioxolan-2''-yl-hexyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester
CAS No.:634911-90-3
Molecular Formula:C₄₈H₆₆N₂O₁₀Si
Molecular Weight:859.145
Hs Code.:

(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyl-diphenyl-silanyloxy)-3'-dimethylcarbamoylmethyl-3'-[1,3]dioxolan-2''-yl-hexyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester

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Chemical Property of (3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyl-diphenyl-silanyloxy)-3'-dimethylcarbamoylmethyl-3'-[1,3]dioxolan-2''-yl-hexyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester

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Technology Process of (3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyl-diphenyl-silanyloxy)-3'-dimethylcarbamoylmethyl-3'-[1,3]dioxolan-2''-yl-hexyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester

There total 15 articles about (3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyl-diphenyl-silanyloxy)-3'-dimethylcarbamoylmethyl-3'-[1,3]dioxolan-2''-yl-hexyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl 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:

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

: 634911-90-3
(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyl-diphenyl-silanyloxy)-3'-dimethylcarbamoylmethyl-3'-[1,3]dioxolan-2''-yl-hexyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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

11: 6.54 g / 4-(dimethylamino)pyridine / acetonitrile / 8 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; acetonitrile; 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

: 634911-90-3
(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyl-diphenyl-silanyloxy)-3'-dimethylcarbamoylmethyl-3'-[1,3]dioxolan-2''-yl-hexyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 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

10: 6.54 g / 4-(dimethylamino)pyridine / acetonitrile / 8 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; acetonitrile; tert-butyl alcohol; benzene; 5: Swern oxidation / 8: Sonogashira coupling;
DOI:10.1016/j.tet.2003.09.005

Reference yield:

: 3-formyl-3-(3-oxo-propyl)-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

: 634911-90-3
(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyl-diphenyl-silanyloxy)-3'-dimethylcarbamoylmethyl-3'-[1,3]dioxolan-2''-yl-hexyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 5.47 g / sodium borohydride / ethanol / 0.33 h / 20 °C

2: 75.3 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.5 h / -5 °C

3: 94.6 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 0.75 h / -65 - 5 °C

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

5: 5.14 g / potassium carbonate / methanol / 2 h / 50 °C

6: 91.7 percent / triethylamine; copper(I) iodide; tetrakis(triphenylphosphine)palladium⁽⁰⁾ / 1 h / 65 °C

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

8: 6.54 g / 4-(dimethylamino)pyridine / acetonitrile / 8 h / 20 °C

With dmap; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetonitrile; benzene; 3: Swern oxidation / 6: Sonogashira coupling;
DOI:10.1016/j.tet.2003.09.005