(1'S,4''S,5R,5''S)-1-benzyl-5-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

Base Information

Chemical Name:(1'S,4''S,5R,5''S)-1-benzyl-5-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one
CAS No.:583039-98-9
Molecular Formula:C₃₁H₄₅NO₅Si
Molecular Weight:539.788
Hs Code.:

Synonyms:(1'S,4''S,5R,5''S)-1-benzyl-5-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

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Chemical Property of (1'S,4''S,5R,5''S)-1-benzyl-5-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

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Technology Process of (1'S,4''S,5R,5''S)-1-benzyl-5-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

There total 5 articles about (1'S,4''S,5R,5''S)-1-benzyl-5-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one 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: 70.0%

: 100-44-7
benzyl chloride

: 583040-18-0
(R)-5-[(S)-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-pyrrolidin-2-one

: 583039-98-9
(1'S,4''S,5R,5''S)-1-benzyl-5-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

Guidance literature:: With potassium hydride; In tetrahydrofuran; at 60 ℃; for 6h;
DOI:10.1021/jo0344539

Reference yield:

: 81028-12-8
(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

: 583039-98-9
(1'S,4''S,5R,5''S)-1-benzyl-5-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / SnCl₄ / diethyl ether; CH₂Cl₂ / 5 h / -80 °C

2: 92 percent / NaBH₄; NiCl₂*6H₂O / methanol / 0.67 h / 0 °C

3: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / Heating

4: 98 percent / ceric ammonium nitrate / acetonitrile / 2 h / Heating

5: 70 percent / KH / tetrahydrofuran; various solvent(s) / 6 h / 60 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; ammonium cerium(IV) nitrate; tin(IV) chloride; potassium hydride; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo0344539

Reference yield:

: 141293-20-1
(1'S,2R,4''S,5''S)-2-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

: 583039-98-9
(1'S,4''S,5R,5''S)-1-benzyl-5-[(benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-(tert-butyldimethylsilanyloxy)methyl]pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / NaBH₄; NiCl₂*6H₂O / methanol / 0.67 h / 0 °C

2: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / Heating

3: 98 percent / ceric ammonium nitrate / acetonitrile / 2 h / Heating

4: 70 percent / KH / tetrahydrofuran; various solvent(s) / 6 h / 60 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; ammonium cerium(IV) nitrate; potassium hydride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo0344539