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

Base Information

Chemical Name:methyl (3S,8R,9S,9aS)-3-(tert-butyldiphenylsilyloxy)methyl-9-hydroxy-8-methoxy-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-9-carboxylate
CAS No.:937206-75-2
Molecular Formula:C₂₉H₃₉NO₆Si
Molecular Weight:525.717
Hs Code.:

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

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

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

There total 8 articles about methyl (3S,8R,9S,9aS)-3-(tert-butyldiphenylsilyloxy)methyl-9-hydroxy-8-methoxy-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-9-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: 74.0%

: 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

: 77-78-1
dimethyl sulfate

: 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

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol070486p

Reference yield:

: 937206-68-3
methyl (2S,3R,3aS,6S)-6-(tert-butyldiphenylsilyloxy)methyl-2-(2-methoxycarbonyl)ethyl-perhydropyrrolo[1,2-b]isoxazole-3-carboxylate

: 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

Guidance literature:: Multi-step reaction with 4 steps

1.1: Zn / acetic acid / 1.5 h

1.2: 84 percent / toluene / 16 h / Heating

2.1: 88 percent / PPh₃; benzoic acid; DIAD / tetrahydrofuran / 1.5 h

3.1: 92 percent / NMO; OsO₄ / 2-methyl-propan-2-ol; acetone; H₂O / 1.5 h / 60 °C

4.1: 74 percent / NaH / tetrahydrofuran / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; di-isopropyl azodicarboxylate; sodium hydride; triphenylphosphine; benzoic acid; zinc; In tetrahydrofuran; water; acetic acid; acetone; tert-butyl alcohol; 2.1: Mitsunobu reaction;
DOI:10.1021/ol070486p

Reference yield:

: 937206-69-4
(S)-2-tert-butyldiphenylsilyloxymethyl-3,4-dihydro-2H-pyrrole-1-oxide

: 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

Guidance literature:: Multi-step reaction with 5 steps

1.1: 78 percent / toluene / 10 h / Heating

2.1: Zn / acetic acid / 1.5 h

2.2: 84 percent / toluene / 16 h / Heating

3.1: 88 percent / PPh₃; benzoic acid; DIAD / tetrahydrofuran / 1.5 h

4.1: 92 percent / NMO; OsO₄ / 2-methyl-propan-2-ol; acetone; H₂O / 1.5 h / 60 °C

5.1: 74 percent / NaH / tetrahydrofuran / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; di-isopropyl azodicarboxylate; sodium hydride; triphenylphosphine; benzoic acid; zinc; In tetrahydrofuran; water; acetic acid; acetone; toluene; tert-butyl alcohol; 3.1: Mitsunobu reaction;
DOI:10.1021/ol070486p