(1R,5R,7S)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]dec-8-en-10-one

Base Information

Chemical Name:(1R,5R,7S)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]dec-8-en-10-one
CAS No.:1437785-08-4
Molecular Formula:C₃₁H₄₀O₃Si
Molecular Weight:488.742
Hs Code.:

Synonyms:(1R,5R,7S)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]dec-8-en-10-one

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Chemical Property of (1R,5R,7S)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]dec-8-en-10-one

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Technology Process of (1R,5R,7S)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]dec-8-en-10-one

There total 10 articles about (1R,5R,7S)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]dec-8-en-10-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:

: (1R,5R)-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-7-hydroxy-6-oxaspiro[4.5]dec-8-en-10-one

: 762-72-1
allyl-trimethyl-silane

: 1437785-08-4
(1R,5R,7S)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]dec-8-en-10-one

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;
DOI:10.1039/c3ob40284c

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1437785-08-4
(1R,5R,7S)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]dec-8-en-10-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

3.1: sodium hydrogencarbonate; sodium acetate; N-Bromosuccinimide / tetrahydrofuran; water / 0.17 h / 0 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; sodium acetate; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane; water; 4.1: |Sakurai Allylation;
DOI:10.1039/c3ob40284c

Reference yield:

: 95514-03-7
(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

: 1437785-08-4
(1R,5R,7S)-7-allyl-1-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-6-oxaspiro[4.5]dec-8-en-10-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 - 20 °C / Inert atmosphere

3.1: triphenylphosphine; zinc / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

4.1: dicobalt octacarbonyl / dichloromethane / 2 h / 20 °C / Inert atmosphere

4.2: 27 °C / Inert atmosphere

5.1: 5%-palladium/activated carbon; hydrogen / ethanol / 2 h / 20 °C / Inert atmosphere

6.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

6.2: -78 °C / Inert atmosphere

7.1: sodium hydrogencarbonate; sodium acetate; N-Bromosuccinimide / tetrahydrofuran; water / 0.17 h / 0 °C / Inert atmosphere

8.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With N-Bromosuccinimide; n-butyllithium; dicobalt octacarbonyl; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; 5%-palladium/activated carbon; boron trifluoride diethyl etherate; hydrogen; sodium acetate; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triphenylphosphine; zinc; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; 2.1: |Swern Oxidation / 3.2: |Corey-Fuchs Alkyne Synthesis / 4.1: |Pauson-Khand Annulation / 8.1: |Sakurai Allylation;
DOI:10.1039/c3ob40284c