(2S,3R)-allyl 2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylate

Base Information

Chemical Name:(2S,3R)-allyl 2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylate
CAS No.:1609691-88-4
Molecular Formula:C₃₈H₆₀O₇Si₂
Molecular Weight:685.061
Hs Code.:

Synonyms:(2S,3R)-allyl 2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylate

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Chemical Property of (2S,3R)-allyl 2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylate

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Technology Process of (2S,3R)-allyl 2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylate

There total 9 articles about (2S,3R)-allyl 2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylate 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:

: 1609691-89-5
allyl 2-[2-{3,4-bis(triisopropylsilyloxy)benzyloxy}-3-(methoxymethoxy)phenyl]-2-diazo acetate

: (2R,3S)-allyl 2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylate

: 1609691-88-4
(2S,3R)-allyl 2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylate

Guidance literature:: With dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate]; In toluene; at -20 ℃; for 1h; Reagent/catalyst; Temperature; Solvent; Overall yield = 81 %; Overall yield = 2.5 g; enantioselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1055/s-0033-1340291

Reference yield:

: C₃₆H₆₂O₇Si₂

: 1609691-88-4
(2S,3R)-allyl 2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

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

2.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / water; diethyl ether; tert-butyl alcohol / 1.5 h

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

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

4.2: 1 h / -78 °C / Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; p-nitrobenzenesulfonyl azide / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

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

With p-nitrobenzenesulfonyl azide; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate]; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1055/s-0033-1340291

Reference yield:

: C₃₅H₅₈O₆Si₂

: 1609691-88-4
(2S,3R)-allyl 2-{3,4-bis(triisopropylsilyloxy)phenyl}-7-(methoxymethoxy)-2,3-dihydrobenzofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 5 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

With p-nitrobenzenesulfonyl azide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate]; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1055/s-0033-1340291