methyl (4aS,8R,8aR)-5-benzyl-8-{2'-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylate

Base Information

Chemical Name:methyl (4aS,8R,8aR)-5-benzyl-8-{2'-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylate
CAS No.:1382154-12-2
Molecular Formula:C₂₅H₃₉NO₇Si
Molecular Weight:493.673
Hs Code.:

Synonyms:methyl (4aS,8R,8aR)-5-benzyl-8-{2'-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylate

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Chemical Property of methyl (4aS,8R,8aR)-5-benzyl-8-{2'-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylate

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Technology Process of methyl (4aS,8R,8aR)-5-benzyl-8-{2'-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylate

There total 17 articles about methyl (4aS,8R,8aR)-5-benzyl-8-{2'-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylate 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%

: 1382153-71-0
(4aS,8R,8aR)-5-benzyl-8-{2'-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylic acid

: 74-88-4
methyl iodide

: 1382154-12-2
methyl (4aS,8R,8aR)-5-benzyl-8-{2'-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylate

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.75h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.04.012

Reference yield:

: 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

: 1382154-12-2
methyl (4aS,8R,8aR)-5-benzyl-8-{2'-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1.25 h / Inert atmosphere; Reflux

2.1: L-Selectride / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

3.2: 23.17 h / 0 - 20 °C / Inert atmosphere

4.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen / ethanol / 15 h / 20 °C / 7600.51 Torr

5.1: 1H-imidazole / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 0.5 h / Inert atmosphere; Reflux

7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; acetonitrile; tert-butyl alcohol / 1 h / 0 °C

8.1: potassium carbonate / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; 20 wt.% Pd(OH)2 on activated carbon; hydrogen; L-Selectride; sodium hydride; potassium carbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; tert-butyl alcohol;
DOI:10.1016/j.tetasy.2012.04.012

Reference yield:

: 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

: 1382154-12-2
methyl (4aS,8R,8aR)-5-benzyl-8-{2'-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

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

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1.25 h / Inert atmosphere; Reflux

3.1: L-Selectride / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

4.2: 23.17 h / 0 - 20 °C / Inert atmosphere

5.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen / ethanol / 15 h / 20 °C / 7600.51 Torr

6.1: 1H-imidazole / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 0.5 h / Inert atmosphere; Reflux

8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; acetonitrile; tert-butyl alcohol / 1 h / 0 °C

9.1: potassium carbonate / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; 20 wt.% Pd(OH)2 on activated carbon; hydrogen; L-Selectride; sodium hydride; potassium carbonate; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; tert-butyl alcohol;
DOI:10.1016/j.tetasy.2012.04.012