(4aR,8S,8aS)-3-Methylene-2-oxo-8-phenylselanyl-2,3,4a,7,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Base Information

Chemical Name:(4aR,8S,8aS)-3-Methylene-2-oxo-8-phenylselanyl-2,3,4a,7,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester
CAS No.:83604-13-1
Molecular Formula:C₁₇H₁₆O₅Se
Molecular Weight:379.271
Hs Code.:

Synonyms:(4aR,8S,8aS)-3-Methylene-2-oxo-8-phenylselanyl-2,3,4a,7,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

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Chemical Property of (4aR,8S,8aS)-3-Methylene-2-oxo-8-phenylselanyl-2,3,4a,7,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

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Technology Process of (4aR,8S,8aS)-3-Methylene-2-oxo-8-phenylselanyl-2,3,4a,7,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

There total 10 articles about (4aR,8S,8aS)-3-Methylene-2-oxo-8-phenylselanyl-2,3,4a,7,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl 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: 37.0%

: 1666-13-3
diphenyl diselenide

: 80631-85-2,86940-67-2,106861-69-2
methyl (1β,5α,6β)-5-<<1-(methoxycarbonyl)ethenyl>oxy>-7-oxabicyclo<4.1.0>hept-3-ene-3-carboxylate

: 83604-13-1
(4aR,8S,8aS)-3-Methylene-2-oxo-8-phenylselanyl-2,3,4a,7,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

: 80631-86-3,86940-68-3,106861-70-5
(3S,4R,5R)-4-Hydroxy-3-(1-methoxycarbonyl-vinyloxy)-5-phenylselanyl-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; for 72h; Ambient temperature;
DOI:10.1021/ja00389a025

Reference yield:

: 4372-89-8,4372-91-2,14671-74-0,16613-43-7,16613-44-8,40983-58-2,121468-33-5,141781-68-2
methyl 4-epi-shikimate

: 83604-13-1
(4aR,8S,8aS)-3-Methylene-2-oxo-8-phenylselanyl-2,3,4a,7,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 72 percent / p-toluenesulfonic acid / toluene / Heating

2: 83 percent / toluene / 1.) 40 deg C, 12 h, 2.) 80 deg C 3 h

3: 50 percent / SOCl₂, pyridine / tetrahydrofuran / 1.) -20 deg C , 0.5 h, 2.) 0 deg C, 1 h

4: 66 percent / N-bromosuccinimide / benzene / Ambient temperature

5: Et₃N / CH₂Cl₂ / 72 h

6: 1.) MeI / 1.) CH₂Cl₂, reflux, 6 h, 2.) Me₂SO, 85-90 deg C, 4 h

7: 46 percent / NaOCH₃ / methanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h, 3.) reflux, 0.75 h

8: 8 percent / NaBH₄ / methanol / 72 h / Ambient temperature

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; thionyl chloride; sodium methylate; toluene-4-sulfonic acid; triethylamine; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;
DOI:10.1021/ja00389a025

Reference yield:

: 83604-12-0
methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate

: 83604-13-1
(4aR,8S,8aS)-3-Methylene-2-oxo-8-phenylselanyl-2,3,4a,7,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 72 h

2: 1.) MeI / 1.) CH₂Cl₂, reflux, 6 h, 2.) Me₂SO, 85-90 deg C, 4 h

3: 46 percent / NaOCH₃ / methanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h, 3.) reflux, 0.75 h

4: 8 percent / NaBH₄ / methanol / 72 h / Ambient temperature

With sodium tetrahydroborate; sodium methylate; triethylamine; methyl iodide; In methanol; dichloromethane;
DOI:10.1021/ja00389a025