(7S,8R,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(7S,8R,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester
CAS No.:946435-52-5
Molecular Formula:C₂₃H₃₁NO₇Se
Molecular Weight:512.462
Hs Code.:

Synonyms:(7S,8R,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester

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Chemical Property of (7S,8R,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester

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Technology Process of (7S,8R,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester

There total 16 articles about (7S,8R,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester 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: 45.0%

: (2S)-3-dimethylaminomethylene-2-[(1R)-3-hydroxy-1-[(2-methoxyethoxy)methoxy]-2-(phenylselanyl)propyl]-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester

: 946435-52-5
(7S,8R,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester

: 946435-59-2
(7R,8R,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester

Guidance literature:: With trifluoroacetic acid; In toluene; at 70 ℃; for 15h;
DOI:10.1021/ol071147z

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 946435-52-5
(7S,8R,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: Et₃N / CH₂Cl₂ / 2.33 h / 0 - 20 °C

2: 94 percent / imidazole / CH₂Cl₂ / 48 h

3: 91 percent / NaBH₄; CaCl₂ / tetrahydrofuran; ethanol / 0 °C

4: 91 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - 20 °C

5: 63 percent / t-BuLi / pentane; tetrahydrofuran / 2 h / -78 °C

6: 83 percent / i-Pr₂NEt; Bu₄NI / tetrahydrofuran / 20 h / Heating

7: 98 percent / ethyl acetate; H₂O / 0.25 h

8: 98 percent / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

9: 80 percent / pyridine; DMAP / CH₂Cl₂ / 3.5 h

10: 95 percent / Bu₄NF; AcOH / tetrahydrofuran / 2 h

11: 40 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1 h / -78 °C

12: 62 percent / K₂CO₃ / methanol; H₂O / 0.5 h

13: 67 percent / tetrahydrofuran / 24 h / Heating

14: 45 percent / CF₃COOH / toluene / 15 h / 70 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; calcium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; toluene; pentane; 4: Swern oxidation / 11: Swern oxidation;
DOI:10.1021/ol071147z

Reference yield:

: 946435-44-5
(2S,4R)-2-[(2Z)-3-ethoxy-1-[(2-methoxyethoxy)methoxy]allyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-carboxylic acid tert-butyl ester

: 946435-52-5
(7S,8R,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / ethyl acetate; H₂O / 0.25 h

2: 98 percent / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

3: 80 percent / pyridine; DMAP / CH₂Cl₂ / 3.5 h

4: 95 percent / Bu₄NF; AcOH / tetrahydrofuran / 2 h

5: 40 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1 h / -78 °C

6: 62 percent / K₂CO₃ / methanol; H₂O / 0.5 h

7: 67 percent / tetrahydrofuran / 24 h / Heating

8: 45 percent / CF₃COOH / toluene / 15 h / 70 °C

With pyridine; dmap; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; toluene; 5: Swern oxidation;
DOI:10.1021/ol071147z