(2S,4R,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-4-methylhexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione

Base Information

Chemical Name:(2S,4R,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-4-methylhexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione
CAS No.:1395833-73-4
Molecular Formula:C₃₁H₄₁NO₅Si
Molecular Weight:535.756
Hs Code.:

(2S,4R,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-4-methylhexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione

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Chemical Property of (2S,4R,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-4-methylhexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione

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Technology Process of (2S,4R,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-4-methylhexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione

There total 4 articles about (2S,4R,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-4-methylhexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione 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:

: 1395833-67-6
(2S,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-1',2',3',7',8',9a'-hexahydro-5H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(6'H)-dione

: 1395833-73-4
(2S,4R,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-4-methylhexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogen; 10% Pd/C / ethanol / 4 h / 760.05 Torr

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

2.2: 0.75 h / -78 °C / Inert atmosphere

With 10% Pd/C; hydrogen; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol;
DOI:10.1021/ol302185j

Reference yield:

: 1395833-69-8
diethyl (2S,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-5,5'-dioxo-1',2',3',5',6',7,'8',9a'-octahydro-5H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin-4-yl}phosphonate

: 1395833-73-4
(2S,4R,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-4-methylhexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium methylate / methanol / 16 h / 20 °C

2.1: hydrogen; 10% Pd/C / ethanol / 4 h / 760.05 Torr

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

3.2: 0.75 h / -78 °C / Inert atmosphere

With 10% Pd/C; hydrogen; sodium methylate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol;
DOI:10.1021/ol302185j

Reference yield:

: 937206-76-3
(3S,8R,9S,9aS)-3-(tert-butyldiphenylsilyloxy)methyl-9-hydroxy-9-hydroxymethyl-8-methoxy-octahydro-5H-pyrrolo[1,2-a]azepin-5-one

: 1395833-73-4
(2S,4R,3'S,8'R,9a'S)-3'-tert-butyldiphenylsilyloxymethyl-8'-methoxy-4-methylhexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepine}-5,5'(4H,6'H)-dione

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydrogencarbonate; potassium carbonate; tetrabutyl-ammonium chloride; N-chloro-succinimide; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane; water / 2 h / 20 °C

2.1: dicyclohexyl-carbodiimide / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

2.2: 0.33 h / 20 °C / Inert atmosphere

3.1: hydrogen; 10% Pd/C / ethanol / 4 h / 760.05 Torr

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

4.2: 0.75 h / -78 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; 10% Pd/C; tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; potassium carbonate; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1021/ol302185j