(2R,3R,4S)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-(5-(tert-butyldiphenylsilyloxy)pent-1-en-2-yl)-5-oxopyrrolidine-1,2-dicarboxylate

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Chemical Name:(2R,3R,4S)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-(5-(tert-butyldiphenylsilyloxy)pent-1-en-2-yl)-5-oxopyrrolidine-1,2-dicarboxylate
CAS No.:848476-38-0
Molecular Formula:C₃₅H₄₇NO₈Si
Molecular Weight:637.846
Hs Code.:

Synonyms:(2R,3R,4S)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-(5-(tert-butyldiphenylsilyloxy)pent-1-en-2-yl)-5-oxopyrrolidine-1,2-dicarboxylate

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Chemical Property of (2R,3R,4S)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-(5-(tert-butyldiphenylsilyloxy)pent-1-en-2-yl)-5-oxopyrrolidine-1,2-dicarboxylate

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Technology Process of (2R,3R,4S)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-(5-(tert-butyldiphenylsilyloxy)pent-1-en-2-yl)-5-oxopyrrolidine-1,2-dicarboxylate

There total 9 articles about (2R,3R,4S)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-(5-(tert-butyldiphenylsilyloxy)pent-1-en-2-yl)-5-oxopyrrolidine-1,2-dicarboxylate 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: 60.0%

: (2R,3R,4R)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-[(1S)-2-hydroxy-1-((3-tert-butyldiphenylsilyloxy)propyl)]-5-oxopyrrolidine-1,2-dicarboxylate

: 848476-38-0
(2R,3R,4S)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-(5-(tert-butyldiphenylsilyloxy)pent-1-en-2-yl)-5-oxopyrrolidine-1,2-dicarboxylate

Guidance literature:: (2R,3R,4R)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-[(1S)-2-hydroxy-1-((3-tert-butyldiphenylsilyloxy)propyl)]-5-oxopyrrolidine-1,2-dicarboxylate; With ortho-nitrophenyl selenocyanate; tributylphosphine; In tetrahydrofuran; at 20 ℃; for 2h;

With pyridine; dihydrogen peroxide; In tetrahydrofuran; at -40 - 20 ℃;
DOI:10.1021/ja042415g

Reference yield:

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

: 848476-38-0
(2R,3R,4S)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-(5-(tert-butyldiphenylsilyloxy)pent-1-en-2-yl)-5-oxopyrrolidine-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / DMAP / CH₂Cl₂ / 18 h

2.1: sodium periodate; aq. ruthenium chloride / ethyl acetate; acetonitrile / 18 h / 20 °C

2.2: 64 percent / methanol; toluene; diethyl ether / 0.08 h

3.1: 71 percent / sodium methoxide / methanol / 1.5 h / -78 °C

4.1: 90 percent / imidazole / CH₂Cl₂ / 18 h

5.1: 100 percent / mCPBA / CH₂Cl₂ / 72 h

6.1: 60 percent / methanol / 1.5 h / -78 °C

7.1: tri-n-butylphosphine; o-nitrophenylselenocyanate / tetrahydrofuran / 2 h / 20 °C

7.2: 60 percent / pyridine; aq. hydrogen peroxide / tetrahydrofuran / -40 - 20 °C

With 1H-imidazole; dmap; ruthenium trichloride; sodium periodate; ortho-nitrophenyl selenocyanate; tributylphosphine; sodium methylate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile; 5.1: Baeyer-Villiger oxidation;
DOI:10.1021/ja042415g

Reference yield:

: 848476-42-6
3-((3R,3aR,7R,7aS)-octahydro-1,5-dioxo-3-phenyl-1H-isoindol-7-yl)propyl formate

: 848476-38-0
(2R,3R,4S)-1-tert-butyl 2-methyl 3-((methoxycarbonyl)methyl)-4-(5-(tert-butyldiphenylsilyloxy)pent-1-en-2-yl)-5-oxopyrrolidine-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / DMAP / CH₂Cl₂ / 18 h

2.1: sodium periodate; aq. ruthenium chloride / ethyl acetate; acetonitrile / 18 h / 20 °C

2.2: 64 percent / methanol; toluene; diethyl ether / 0.08 h

3.1: 71 percent / sodium methoxide / methanol / 1.5 h / -78 °C

4.1: 90 percent / imidazole / CH₂Cl₂ / 18 h

5.1: 100 percent / mCPBA / CH₂Cl₂ / 72 h

6.1: 60 percent / methanol / 1.5 h / -78 °C

7.1: tri-n-butylphosphine; o-nitrophenylselenocyanate / tetrahydrofuran / 2 h / 20 °C

7.2: 60 percent / pyridine; aq. hydrogen peroxide / tetrahydrofuran / -40 - 20 °C

With 1H-imidazole; dmap; ruthenium trichloride; sodium periodate; ortho-nitrophenyl selenocyanate; tributylphosphine; sodium methylate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile; 5.1: Baeyer-Villiger oxidation;
DOI:10.1021/ja042415g