(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester
CAS No.:545363-26-6
Molecular Formula:C₄₈H₆₃NO₁₁Si
Molecular Weight:858.114
Hs Code.:

(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester

Synonyms:(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester

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Chemical Property of (3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester

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Technology Process of (3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester

There total 10 articles about (3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-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: 94.3%

: 24424-99-5
di-tert-butyl dicarbonate

: 545362-99-0
(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-dimethoxymethyl-pent-4-ynoic acid ethyl ester

: 545363-26-6
(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester

Guidance literature:: With dmap; In acetonitrile; at 20 ℃; for 0.25h;
DOI:10.1016/j.tet.2003.09.005 DOI:10.1021/ol034445e

Reference yield:

: 55149-84-3
2-nitroveratraldehyde

: 545363-26-6
(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 80.5 percent / n-Bu₄N⁽¹⁺⁾*I^(1-); NaOH / H₂O; CH₂Cl₂ / 0.42 h / 5 °C

2.1: Zn; AcOH / CH₂Cl₂ / 10 - 20 °C

3.1: Ac₂O / CH₂Cl₂ / 0.17 h / 5 °C

4.1: 63.3 percent / pyridine; phosphopus oxychloride / CH₂Cl₂ / 1.17 h / 5 °C

5.1: Bu₃SnH; AIBN / acetonitrile / 1.5 h / Heating

5.2: 84.6 percent / I₂ / acetonitrile / 1 h / 20 °C

6.1: 12.5 g / DIBAL / toluene / 0.83 h / 5 °C

7.1: 85.3 percent / pyridine / 0.5 h

8.1: 78 percent / triethylamine; Pd(PPh₃)4; CuI / 2 h / 70 °C

9.1: 94.3 percent / 4-(dimethylamino)pyridine / acetonitrile / 0.25 h / 20 °C

With pyridine; dmap; sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; acetic anhydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; acetic acid; triethylamine; zinc; trichlorophosphate; In dichloromethane; water; toluene; acetonitrile; 1.1: Wittig olefination / 8.1: Sonogashira coupling;
DOI:10.1021/ol034445e

Reference yield:

: 545363-22-2
(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-pent-4-ynoic acid ethyl ester

: 545363-26-6
(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: DMSO; (COCl)2; triethylamine / CH₂Cl₂ / -78 - 20 °C

2: 2.35 g / camphorsulfonic acid / methanol / 0.5 h / 20 °C

3: 78 percent / triethylamine; Pd(PPh₃)4; CuI / 2 h / 70 °C

4: 94.3 percent / 4-(dimethylamino)pyridine / acetonitrile / 0.25 h / 20 °C

With dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; acetonitrile; 1: Swern oxidation / 3: Sonogashira coupling;
DOI:10.1021/ol034445e