(3aR,4'S,5R,6aR)-3-benzyl-5-[3-(benzyloxy)propyl]-2,2-dimethyldihydro-3aHspiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

Base Information

Chemical Name:(3aR,4'S,5R,6aR)-3-benzyl-5-[3-(benzyloxy)propyl]-2,2-dimethyldihydro-3aHspiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one
CAS No.:1315158-46-3
Molecular Formula:C₂₆H₃₁NO₆
Molecular Weight:453.535
Hs Code.:

Synonyms:(3aR,4'S,5R,6aR)-3-benzyl-5-[3-(benzyloxy)propyl]-2,2-dimethyldihydro-3aHspiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

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Chemical Property of (3aR,4'S,5R,6aR)-3-benzyl-5-[3-(benzyloxy)propyl]-2,2-dimethyldihydro-3aHspiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

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Technology Process of (3aR,4'S,5R,6aR)-3-benzyl-5-[3-(benzyloxy)propyl]-2,2-dimethyldihydro-3aHspiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

There total 3 articles about (3aR,4'S,5R,6aR)-3-benzyl-5-[3-(benzyloxy)propyl]-2,2-dimethyldihydro-3aHspiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-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: 95.0%

: 1315158-43-0
(3aR,4'S,5R,6aR)-5-(3-hydroxypropyl)-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

: 100-39-0
benzyl bromide

: 1315158-46-3
(3aR,4'S,5R,6aR)-3-benzyl-5-[3-(benzyloxy)propyl]-2,2-dimethyldihydro-3aHspiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

Guidance literature:: (3aR,4'S,5R,6aR)-5-(3-hydroxypropyl)-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.25h; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 3.16h; Inert atmosphere;
DOI:10.2478/s11696-011-0030-5

Reference yield:

: 1315158-40-7
ethyl 3-{(3aR,4'S,5R,6aR)-2,2-dimethyl-2'-oxodihydro-3aH-spiro[furo[2,3-d][1,3]-dioxole-6,4'-oxazolidine]-5-yl}propanoate

: 1315158-46-3
(3aR,4'S,5R,6aR)-3-benzyl-5-[3-(benzyloxy)propyl]-2,2-dimethyldihydro-3aHspiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -15 °C / Inert atmosphere

1.2: 2 h / -15 - -5 °C / Inert atmosphere

1.3: 0.5 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

2.2: 3.16 h / 0 - 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.2478/s11696-011-0030-5

Reference yield:

: ethyl-3-{(3aR,4'S,5R,6aR)-2,2-dimethyl-2'-oxodihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidine]-5-yl}acrylate

: 1315158-46-3
(3aR,4'S,5R,6aR)-3-benzyl-5-[3-(benzyloxy)propyl]-2,2-dimethyldihydro-3aHspiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / ethanol / 16 h / 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -15 °C / Inert atmosphere

2.2: 2 h / -15 - -5 °C / Inert atmosphere

2.3: 0.5 h / 20 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

3.2: 3.16 h / 0 - 20 °C / Inert atmosphere

With palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; sodium hydride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.2478/s11696-011-0030-5