(3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone

Base Information

Chemical Name:(3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone
CAS No.:137664-49-4
Molecular Formula:C₁₄H₂₃NO₆
Molecular Weight:301.34
Hs Code.:

Synonyms:(3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone

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Chemical Property of (3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone

Chemical Property:

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Technology Process of (3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone

There total 1 articles about (3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone 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

: 137664-49-4
(3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 12 steps

1: 72 percent / TsOH

2: LDA

3: aq. H₂O₂

4: OsO₄; NMO

5: TsOH / acetone

6: 73 percent / NH₂NH₂; 10 percent Pd/C / methanol / Heating

7: NaH / tetrahydrofuran; dimethylformamide

8: H₂ / Pd(OH)2 / ethanol / 2585.74 Torr

9: 97 percent / NaH / tetrahydrofuran; dimethylformamide

10: 24 percent / aq. cerium(IV) ammonium nitrate / acetonitrile

11: 80 percent / aq. LiOOH / tetrahydrofuran

12: 90 percent / DMAP / tetrahydrofuran / Heating

With dmap; palladium on activated charcoal; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; lithium hydroperoxide; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; hydrazine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetone; acetonitrile; 1: Cyclization / 2: Metallation / 2: selenylation / 3: oxidative olefination / 4: Oxidation / 5: transacetalization / 6: Ring cleavage / 7: protection / 8: Hydrogenolysis / 9: Methylation / 10: deprotection / 11: Hydrolysis / 12: Acylation;
DOI:10.1021/ja992135e

Reference yield: 70.0%

: 137664-49-4
(3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone

: (R)-3-(4-Benzyloxymethyl-oxazol-2-yl)-butylamine

: ((R)-1-{(4R,5R)-5-[(R)-3-(4-Benzyloxymethyl-oxazol-2-yl)-butylcarbamoyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxy-ethyl)-carbamic acid tert-butyl ester

Guidance literature:: With trimethylaluminum; In benzene;
DOI:10.1021/ja992135e

Reference yield:

: 137664-49-4
(3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxymethyl-2-pyrrolidinone

: (2R,3R,4R)-4-Dimethylamino-2,3-dihydroxy-5-methoxy-pentanoic acid benzylamide

Guidance literature:: Multi-step reaction with 4 steps

1: LiOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

2: diphenyl phosphorazidate, Et₃N / dimethylformamide / 1) 1h, 0 deg C 2) 41h, r.t.

3: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

4: H₂, AcOH / 5percent Pd/C / methanol; H₂O / 60 h / Ambient temperature

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)79444-5