(2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(salicylic alcohol isopropylideneacetal-6-yl)-5-oxopyrrolidin-1-carboxylate

Base Information

Chemical Name:(2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(salicylic alcohol isopropylideneacetal-6-yl)-5-oxopyrrolidin-1-carboxylate
CAS No.:1622235-70-4
Molecular Formula:C₂₆H₄₁NO₆Si
Molecular Weight:491.7
Hs Code.:

Synonyms:(2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(salicylic alcohol isopropylideneacetal-6-yl)-5-oxopyrrolidin-1-carboxylate

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Chemical Property of (2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(salicylic alcohol isopropylideneacetal-6-yl)-5-oxopyrrolidin-1-carboxylate

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Technology Process of (2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(salicylic alcohol isopropylideneacetal-6-yl)-5-oxopyrrolidin-1-carboxylate

There total 1 articles about (2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(salicylic alcohol isopropylideneacetal-6-yl)-5-oxopyrrolidin-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:

: 17342-08-4
(S)-Pyroglutaminol

: 1622235-70-4
(2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(salicylic alcohol isopropylideneacetal-6-yl)-5-oxopyrrolidin-1-carboxylate

Guidance literature:: Multi-step reaction with 4 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 / pentane; diethyl ether / 0.58 h / -78 °C / Inert atmosphere

4.2: 0.25 h / -78 - -42 °C / Inert atmosphere

4.3: 1 h / -78 - -42 °C / Inert atmosphere

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

Reference yield:

: 1622235-70-4
(2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(salicylic alcohol isopropylideneacetal-6-yl)-5-oxopyrrolidin-1-carboxylate

: 1622235-64-6
(2S,3R)-3-(3-carboxy-4-hydroxyphenyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: borane-THF / tetrahydrofuran / 3.5 h / 80 °C / Inert atmosphere

1.2: 3.5 h / 0 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: sodium periodate; ruthenium(III) trichloride hydrate / water; ethyl acetate; acetonitrile / 1.5 h / 0 °C

4.1: water / 20 °C

With sodium periodate; borane-THF; ruthenium(III) trichloride hydrate; tetrabutyl ammonium fluoride; In tetrahydrofuran; water; ethyl acetate; acetonitrile;

Reference yield:

: 1622235-70-4
(2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(salicylic alcohol isopropylideneacetal-6-yl)-5-oxopyrrolidin-1-carboxylate

: 1622235-61-3
C₁₇H₂₅NO₅

Guidance literature:: Multi-step reaction with 2 steps

1.1: borane-THF / tetrahydrofuran / 3.5 h / 80 °C / Inert atmosphere

1.2: 3.5 h / 0 - 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid; methanol / 5 h / 20 °C

With methanol; borane-THF; toluene-4-sulfonic acid; In tetrahydrofuran;