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

Base Information

Chemical Name:(3S,8R,9S,9aS)-3-(tert-butyldiphenylsilyloxy)methyl-9-hydroxy-9-hydroxymethyl-8-methoxy-octahydro-5H-pyrrolo[1,2-a]azepin-5-one
CAS No.:937206-76-3
Molecular Formula:C₂₈H₃₉NO₅Si
Molecular Weight:497.707
Hs Code.:

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

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

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

There total 9 articles about (3S,8R,9S,9aS)-3-(tert-butyldiphenylsilyloxy)methyl-9-hydroxy-9-hydroxymethyl-8-methoxy-octahydro-5H-pyrrolo[1,2-a]azepin-5-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: 97.0%

: 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

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

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 18h;
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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With lithium borohydride; sodium hydride; In tetrahydrofuran;
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

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

Guidance literature:: Multi-step reaction with 5 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

5.1: 97 percent / LiBH₄ / tetrahydrofuran / 18 h / 20 °C

With osmium(VIII) oxide; lithium borohydride; 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