(5R,6S)-1-benzyl-6-[(E)-3'-hydroxyprop-1'-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

Base Information

Chemical Name:(5R,6S)-1-benzyl-6-[(E)-3'-hydroxyprop-1'-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one
CAS No.:1382153-75-4
Molecular Formula:C₁₈H₂₃NO₅
Molecular Weight:333.384
Hs Code.:

Synonyms:(5R,6S)-1-benzyl-6-[(E)-3'-hydroxyprop-1'-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

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Chemical Property of (5R,6S)-1-benzyl-6-[(E)-3'-hydroxyprop-1'-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

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Technology Process of (5R,6S)-1-benzyl-6-[(E)-3'-hydroxyprop-1'-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

There total 8 articles about (5R,6S)-1-benzyl-6-[(E)-3'-hydroxyprop-1'-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-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:

: 1382153-78-7
(3aR,4'S,5S,6aR)-3'-benzyl-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

: 1382153-75-4
(5R,6S)-1-benzyl-6-[(E)-3'-hydroxyprop-1'-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: pyridine; dmap / 0.5 h / 20 °C / Inert atmosphere

3.1: water; trifluoroacetic acid / 8.5 h / 20 °C / Inert atmosphere

4.1: benzoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

5.2: 1.5 h / 0 - 20 °C

6.1: sodium periodate / methanol; water / 0.5 h / 20 °C / Inert atmosphere

7.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 - 20 °C / Inert atmosphere

8.1: camphor-10-sulfonic acid / 1 h / 40 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; benzoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; 4.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.04.012

Reference yield:

: 1382153-86-7
ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate

: 1382153-75-4
(5R,6S)-1-benzyl-6-[(E)-3'-hydroxyprop-1'-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

1.2: 1.5 h / 0 - 20 °C

2.1: sodium periodate / methanol; water / 0.5 h / 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 - 20 °C / Inert atmosphere

4.1: camphor-10-sulfonic acid / 1 h / 40 °C / Inert atmosphere

With sodium tetrahydroborate; sodium periodate; camphor-10-sulfonic acid; diisobutylaluminium hydride; In methanol; ethanol; dichloromethane; water; toluene;
DOI:10.1016/j.tetasy.2012.04.012

Reference yield:

: 1382153-84-5
(5R,6S,8S,9R)-6-(acetoxymethyl)-1-benzyl-8,9-dihydroxy-3,7-dioxa-1-azaspiro [4.4]nonan-2-one

: 1382153-75-4
(5R,6S)-1-benzyl-6-[(E)-3'-hydroxyprop-1'-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: benzoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

2.2: 1.5 h / 0 - 20 °C

3.1: sodium periodate / methanol; water / 0.5 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 - 20 °C / Inert atmosphere

5.1: camphor-10-sulfonic acid / 1 h / 40 °C / Inert atmosphere

With sodium tetrahydroborate; sodium periodate; camphor-10-sulfonic acid; diisobutylaluminium hydride; benzoic acid; In methanol; ethanol; dichloromethane; water; toluene; 1.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.04.012