(5R,6R)-1-benzyl-6-{(1'S)-3'-[(tert-butyldimethylsilyl)oxy]-1'-hydroxypropyl}-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

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Chemical Name:(5R,6R)-1-benzyl-6-{(1'S)-3'-[(tert-butyldimethylsilyl)oxy]-1'-hydroxypropyl}-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one
CAS No.:1382153-73-2
Molecular Formula:C₂₄H₃₉NO₆Si
Molecular Weight:465.662
Hs Code.:

Synonyms:(5R,6R)-1-benzyl-6-{(1'S)-3'-[(tert-butyldimethylsilyl)oxy]-1'-hydroxypropyl}-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

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Chemical Property of (5R,6R)-1-benzyl-6-{(1'S)-3'-[(tert-butyldimethylsilyl)oxy]-1'-hydroxypropyl}-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

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Technology Process of (5R,6R)-1-benzyl-6-{(1'S)-3'-[(tert-butyldimethylsilyl)oxy]-1'-hydroxypropyl}-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

There total 10 articles about (5R,6R)-1-benzyl-6-{(1'S)-3'-[(tert-butyldimethylsilyl)oxy]-1'-hydroxypropyl}-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: 65.0%

: 1382153-98-1
(5R,6R)-1-benzyl-6-[(1'S)-1',3'-dihydroxypropyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1382153-73-2
(5R,6R)-1-benzyl-6-{(1'S)-3'-[(tert-butyldimethylsilyl)oxy]-1'-hydroxypropyl}-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

Guidance literature:: With dmap; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.04.012

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

: 1382153-73-2
(5R,6R)-1-benzyl-6-{(1'S)-3'-[(tert-butyldimethylsilyl)oxy]-1'-hydroxypropyl}-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

Guidance literature:: Multi-step reaction with 11 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

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere

10.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / 0 °C / Inert atmosphere

10.2: 1 h / 20 °C

11.1: dmap; triethylamine / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; benzoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 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

: 1382153-73-2
(5R,6R)-1-benzyl-6-{(1'S)-3'-[(tert-butyldimethylsilyl)oxy]-1'-hydroxypropyl}-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one

Guidance literature:: Multi-step reaction with 7 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

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere

6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / 0 °C / Inert atmosphere

6.2: 1 h / 20 °C

7.1: dmap; triethylamine / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; sodium periodate; camphor-10-sulfonic acid; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tetasy.2012.04.012