(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate

Base Information

Chemical Name:(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate
CAS No.:1622235-76-0
Molecular Formula:C₃₆H₅₉NO₅Si₂
Molecular Weight:642.039
Hs Code.:

(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate

Synonyms:(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate

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Chemical Property of (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate

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Technology Process of (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate

There total 12 articles about (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-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: 60.0%

: 1622235-72-6
(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate

: 1622235-76-0
(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate

Guidance literature:: (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate; With borane-THF; In tetrahydrofuran; for 20h; Inert atmosphere; Reflux;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/acs.jmedchem.5b00750

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 1622235-76-0
(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole / dichloromethane / 24 h / 20 °C

2.1: dmap / acetonitrile / 0 - 20 °C

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

3.2: 0.75 h / -78 °C

3.3: 1.41 h / 0 - 20 °C

4.1: tert.-butyl lithium / diethyl ether / 0.75 h / -78 °C / Inert atmosphere

4.2: 0.42 h / -78 - -42 °C / Inert atmosphere

5.1: borane-THF / tetrahydrofuran / 20.08 h / Inert atmosphere; Reflux

5.2: 0.5 h / 0 °C / Inert atmosphere

5.3: 1.33 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; borane-THF; tert.-butyl lithium; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1622235-76-0
(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: potassium carbonate / acetone / 24 h / Reflux

2.2: 2.5 h / Reflux

3.1: tert.-butyl lithium / diethyl ether / 0.75 h / -78 °C / Inert atmosphere

3.2: 0.42 h / -78 - -42 °C / Inert atmosphere

4.1: borane-THF / tetrahydrofuran / 20.08 h / Inert atmosphere; Reflux

4.2: 0.5 h / 0 °C / Inert atmosphere

4.3: 1.33 h / 20 °C / Inert atmosphere

With borane-THF; tert.-butyl lithium; potassium carbonate; In tetrahydrofuran; diethyl ether; acetone;