(2R,3'S,8'R,9a'S)-3'-(tert-butyldiphenylsilyloxy)methyl-8'-methoxy-4-methylenehexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin}-5,5'(4H,6'H)-dione

Base Information

Chemical Name:(2R,3'S,8'R,9a'S)-3'-(tert-butyldiphenylsilyloxy)methyl-8'-methoxy-4-methylenehexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin}-5,5'(4H,6'H)-dione
CAS No.:937206-77-4
Molecular Formula:C₃₁H₃₉NO₅Si
Molecular Weight:533.74
Hs Code.:

(2R,3'S,8'R,9a'S)-3'-(tert-butyldiphenylsilyloxy)methyl-8'-methoxy-4-methylenehexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin}-5,5'(4H,6'H)-dione

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

Chemical Property:

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

There total 10 articles about (2R,3'S,8'R,9a'S)-3'-(tert-butyldiphenylsilyloxy)methyl-8'-methoxy-4-methylenehexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin}-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:

: 937206-75-2
methyl (3S,8R,9S,9aS)-3-(tert-butyldiphenylsilyloxy)methyl-9-hydroxy-8-methoxy-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-9-carboxylate

: 937206-77-4
(2R,3'S,8'R,9a'S)-3'-(tert-butyldiphenylsilyloxy)methyl-8'-methoxy-4-methylenehexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin}-5,5'(4H,6'H)-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / LiBH₄ / tetrahydrofuran / 18 h / 20 °C

2: 92 percent / lead tetraacetate / tetrahydrofuran / 1.5 h / 20 °C

3: 86 percent / Zn / tetrahydrofuran / 1 h / Heating

With lead(IV) acetate; lithium borohydride; zinc; In tetrahydrofuran;
DOI:10.1021/ol070486p

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

: 937206-77-4
(2R,3'S,8'R,9a'S)-3'-(tert-butyldiphenylsilyloxy)methyl-8'-methoxy-4-methylenehexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin}-5,5'(4H,6'H)-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / lead tetraacetate / tetrahydrofuran / 1.5 h / 20 °C

2: 86 percent / Zn / tetrahydrofuran / 1 h / Heating

With lead(IV) acetate; zinc; In tetrahydrofuran;
DOI:10.1021/ol070486p

Reference yield:

: 937206-73-0
methyl (3S,8R,9S,9aS)-3-(tert-butyldiphenylsilyloxy)methyl-8,9-dihydroxy-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-9-carboxylate

: 937206-77-4
(2R,3'S,8'R,9a'S)-3'-(tert-butyldiphenylsilyloxy)methyl-8'-methoxy-4-methylenehexahydro-3H-spiro{furan-2,9'-pyrrolo[1,2-a]azepin}-5,5'(4H,6'H)-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 74 percent / NaH / tetrahydrofuran / 20 °C

2: 97 percent / LiBH₄ / tetrahydrofuran / 18 h / 20 °C

3: 92 percent / lead tetraacetate / tetrahydrofuran / 1.5 h / 20 °C

4: 86 percent / Zn / tetrahydrofuran / 1 h / Heating

With lead(IV) acetate; lithium borohydride; sodium hydride; zinc; In tetrahydrofuran;
DOI:10.1021/ol070486p