benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate
CAS No.:1400145-09-6
Molecular Formula:C₃₃H₃₇NO₅Si
Molecular Weight:555.746
Hs Code.:

Synonyms:benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate

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Chemical Property of benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate

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Technology Process of benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate

There total 3 articles about benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-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:

: 61550-02-5
(furan-2-yloxy)-trimethylsilane

: 245648-29-7
benzyl (2S,5RS)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-methoxypyrrolidine-1-carboxylate

: 1400145-08-5
benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate

: 1400145-09-6
benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate

Guidance literature:: (furan-2-yloxy)-trimethylsilane; benzyl (2S,5RS)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-methoxypyrrolidine-1-carboxylate; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere;

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h; Overall yield = 97 %; Overall yield = 2.32 g; Inert atmosphere;
DOI:10.1021/jo3014484

Reference yield:

: 245648-28-6
(S)-benzyl 2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate

: 1400145-08-5
benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate

: 1400145-09-6
benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / 0.5 h / -45 °C / Inert atmosphere

2.1: camphor-10-sulfonic acid / 2 h / 0 °C

3.1: dichloromethane / 0.25 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

With camphor-10-sulfonic acid; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo3014484

Reference yield:

: 245674-39-9
(5S)-1-(benzyloxycarbonyl)-5-[(tert-butyldiphenylsilyloxy)methyl]-2-hydroxypyrrolidine

: 1400145-08-5
benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate

: 1400145-09-6
benzyl (2S,5S)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(5-oxo-2,5-dihydrofuran-2-yl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: camphor-10-sulfonic acid / 2 h / 0 °C

2.1: dichloromethane / 0.25 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

With camphor-10-sulfonic acid; In dichloromethane;
DOI:10.1021/jo3014484