(3aR,6R,6aR)-6-Hydroxymethyl-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

Base Information

Chemical Name:(3aR,6R,6aR)-6-Hydroxymethyl-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one
CAS No.:137664-62-1
Molecular Formula:C₁₆H₂₁NO₅
Molecular Weight:307.346
Hs Code.:

Synonyms:(3aR,6R,6aR)-6-Hydroxymethyl-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

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Chemical Property of (3aR,6R,6aR)-6-Hydroxymethyl-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

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Technology Process of (3aR,6R,6aR)-6-Hydroxymethyl-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

There total 19 articles about (3aR,6R,6aR)-6-Hydroxymethyl-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-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:

: 17342-08-4
(S)-Pyroglutaminol

: 137664-62-1
(3aR,6R,6aR)-6-Hydroxymethyl-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

Guidance literature:: Multi-step reaction with 8 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

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

Reference yield:

: 254442-10-9
(3aR,6R,6aR)-5-(4-Methoxy-benzyl)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

: 137664-62-1
(3aR,6R,6aR)-6-Hydroxymethyl-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

Guidance literature:: With hydrogen; palladium dihydroxide; In ethanol; under 2585.74 Torr;
DOI:10.1021/ja992135e

Reference yield:

: (3aR,6R,6aR)-6-((Z)-3,3-Dimethyl-2-trimethylsilanyloxy-but-1-enyl)-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

: 137664-62-1
(3aR,6R,6aR)-6-Hydroxymethyl-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one

Guidance literature:: With sodium tetrahydroborate; ozone; Yield given. Multistep reaction; 2) CH₂Cl₂, MeOH, -78 deg C to 0 deg C;
DOI:10.1016/S0040-4039(00)93480-4