(2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-4-{(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-en-1-yl}-2,3-dihydrobenzofuran-3-carboxylic acid

Base Information

Chemical Name:(2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-4-{(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-en-1-yl}-2,3-dihydrobenzofuran-3-carboxylic acid
CAS No.:1609691-87-3
Molecular Formula:C₄₀H₅₉Cl₃O₉Si₂
Molecular Weight:846.433
Hs Code.:

(2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-4-{(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-en-1-yl}-2,3-dihydrobenzofuran-3-carboxylic acid

Synonyms:(2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-4-{(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-en-1-yl}-2,3-dihydrobenzofuran-3-carboxylic acid

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Chemical Property of (2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-4-{(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-en-1-yl}-2,3-dihydrobenzofuran-3-carboxylic acid

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Technology Process of (2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-4-{(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-en-1-yl}-2,3-dihydrobenzofuran-3-carboxylic acid

There total 12 articles about (2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-4-{(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-en-1-yl}-2,3-dihydrobenzofuran-3-carboxylic acid 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: 51.0%

: 44925-09-9
acrylate de trichloro-2,2,2 ethyle

: 1609691-94-2
(2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylic acid

: 1609691-87-3
(2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-4-{(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-en-1-yl}-2,3-dihydrobenzofuran-3-carboxylic acid

Guidance literature:: With tert-Amyl alcohol; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen; palladium diacetate; potassium hydrogencarbonate; at 50 ℃; for 8h; under 760.051 Torr;
DOI:10.1055/s-0033-1340291

Reference yield:

: 1126-20-1
2-allyloxyphenol

: 1609691-87-3
(2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-4-{(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-en-1-yl}-2,3-dihydrobenzofuran-3-carboxylic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 6 h / 50 °C / Inert atmosphere

2.1: 18 h / 180 °C / Microwave irradiation; Inert atmosphere

3.1: diethylazodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran; diethyl ether / 6 h / 0 - 20 °C / Inert atmosphere

4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; diethyl ether; tert-butyl alcohol / 3 h / 0 - 20 °C

5.1: sodium periodate / water; diethyl ether / 6 h / 0 - 20 °C

6.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / water; diethyl ether; tert-butyl alcohol / 1.5 h

7.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 2 °C / Inert atmosphere

8.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

8.2: 1 h / -78 °C / Inert atmosphere

9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; p-nitrobenzenesulfonyl azide / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

10.1: dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] / toluene / 1 h / -20 °C / Molecular sieve; Inert atmosphere

11.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium tetrahydroborate / methanol; tetrahydrofuran / 0 - 20 °C / Inert atmosphere

12.1: tert-Amyl alcohol; palladium diacetate; potassium hydrogencarbonate; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen / 8 h / 50 °C / 760.05 Torr

With p-nitrobenzenesulfonyl azide; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert-Amyl alcohol; 2-methyl-but-2-ene; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate]; oxygen; palladium diacetate; potassium hydrogencarbonate; caesium carbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 2.1: |Claisen Rearrangement / 3.1: |Mitsunobu Displacement;
DOI:10.1055/s-0033-1340291

Reference yield:

: C₃₅H₅₈O₆Si₂

: 1609691-87-3
(2S,3R)-2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-4-{(E)-3-oxo-3-(2,2,2-trichloroethoxy)prop-1-en-1-yl}-2,3-dihydrobenzofuran-3-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / water; diethyl ether; tert-butyl alcohol / 1.5 h

2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 2 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; p-nitrobenzenesulfonyl azide / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

5.1: dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] / toluene / 1 h / -20 °C / Molecular sieve; Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium tetrahydroborate / methanol; tetrahydrofuran / 0 - 20 °C / Inert atmosphere

7.1: tert-Amyl alcohol; palladium diacetate; potassium hydrogencarbonate; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen / 8 h / 50 °C / 760.05 Torr

With p-nitrobenzenesulfonyl azide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert-Amyl alcohol; 2-methyl-but-2-ene; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate]; oxygen; palladium diacetate; potassium hydrogencarbonate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1055/s-0033-1340291