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

Base Information

Chemical Name: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
CAS No.:1395833-69-8
Molecular Formula:C₃₄H₄₆NO₈PSi
Molecular Weight:655.8
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 1 articles about 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 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: 23.0%

: 3095-95-2
diethylphosphonoacetic acid

: 1395833-50-7
(3S,8R,9S,9aS)-3-tert-butyldiphenylsilyloxymethyl-9-hydroxy-8-methoxy-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-9-carbaldehyde

: 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

: 1395833-69-8
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

Guidance literature:: diethylphosphonoacetic acid; (3S,8R,9S,9aS)-3-tert-butyldiphenylsilyloxymethyl-9-hydroxy-8-methoxy-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-9-carbaldehyde; With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 1.5h; Inert atmosphere;

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.333333h; Inert atmosphere;
DOI:10.1021/ol302185j

Reference yield: 93.0%

: 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

: 1395833-67-6
(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

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 16h;
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

: 1395833-71-2
(2S,3'S,8'R,9a'S)-3'-tert-butyl-diphenylsilyloxymethyl-8'-methoxy-hexahydro-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: sodium methylate / methanol / 16 h / 20 °C

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

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