diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methylpyrrolidin-2-ylidene]malonate

Base Information

Chemical Name:diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methylpyrrolidin-2-ylidene]malonate
CAS No.:560130-14-5
Molecular Formula:C₃₂H₄₅NO₇Si
Molecular Weight:583.797
Hs Code.:

Synonyms:diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methylpyrrolidin-2-ylidene]malonate

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Chemical Property of diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methylpyrrolidin-2-ylidene]malonate

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Technology Process of diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methylpyrrolidin-2-ylidene]malonate

There total 12 articles about diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methylpyrrolidin-2-ylidene]malonate 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: 82.0%

: 685-87-0
Diethyl 2-bromomalonate

: 157831-29-3
(3S,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methyl-pyrrolidin-2-thione

: 560130-14-5
diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methylpyrrolidin-2-ylidene]malonate

Guidance literature:: Diethyl 2-bromomalonate; (3S,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methyl-pyrrolidin-2-thione; In dichloromethane; at 20 ℃; for 5h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 3h;

With triphenylphosphine; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1016/S0040-4020(03)00378-8

Reference yield:

: 60933-68-8
3,4,6-tri-O-benzyl-β-D-arabinofuranoside

: 560130-14-5
diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methylpyrrolidin-2-ylidene]malonate

Guidance literature:: Multi-step reaction with 8 steps

1.1: toluene / 12 h / Heating

2.1: 23.7 g / tetrahydrofuran / 12.5 h / 0 - 20 °C

3.1: 71 percent / PCC; molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h / 20 °C

4.1: O₃/O₂ / ethanol / 0.33 h / -25 °C

4.2: 98 percent / NaBH₄ / ethanol / 0.33 h / 20 °C

5.1: 99 percent / ammonium cerium (IV) nitrate / acetonitrile; H₂O / 1 h / 20 °C

6.1: 89 percent / imidazole / dimethylformamide / 1 h / 20 °C

7.1: 97 percent / Lawesson's reagent / toluene / 0.67 h / 60 °C

8.1: CH₂Cl₂ / 5 h / 20 °C

8.2: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 3 h

8.3: 82 percent / triphenylphosphine / CH₂Cl₂ / 5 h / 20 °C

With Lawessons reagent; 1H-imidazole; ammonium cerium(IV) nitrate; 4 A molecular sieve; oxygen; ozone; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(03)00378-8

Reference yield:

: 157831-27-1
(3S,4R,5S)-3,4-dibenzyloxy-5-hydroxymethyl-1-(4-methoxyphenyl)methyl-pyrrolidin-2-one

: 560130-14-5
diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methylpyrrolidin-2-ylidene]malonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / ammonium cerium (IV) nitrate / acetonitrile; H₂O / 1 h / 20 °C

2.1: 89 percent / imidazole / dimethylformamide / 1 h / 20 °C

3.1: 97 percent / Lawesson's reagent / toluene / 0.67 h / 60 °C

4.1: CH₂Cl₂ / 5 h / 20 °C

4.2: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 3 h

4.3: 82 percent / triphenylphosphine / CH₂Cl₂ / 5 h / 20 °C

With Lawessons reagent; 1H-imidazole; ammonium cerium(IV) nitrate; In dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(03)00378-8