(-)-Methyl (3α,4β,5α)-3,5-dihydroxy-4-(phenylseleno)-1-cyclohexene-1-carboxylate

Base Information

Chemical Name:(-)-Methyl (3α,4β,5α)-3,5-dihydroxy-4-(phenylseleno)-1-cyclohexene-1-carboxylate
CAS No.:119999-50-7
Molecular Formula:C₁₄H₁₆O₄Se
Molecular Weight:327.239
Hs Code.:

Synonyms:(-)-Methyl (3α,4β,5α)-3,5-dihydroxy-4-(phenylseleno)-1-cyclohexene-1-carboxylate

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Chemical Property of (-)-Methyl (3α,4β,5α)-3,5-dihydroxy-4-(phenylseleno)-1-cyclohexene-1-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of (-)-Methyl (3α,4β,5α)-3,5-dihydroxy-4-(phenylseleno)-1-cyclohexene-1-carboxylate

There total 1 articles about (-)-Methyl (3α,4β,5α)-3,5-dihydroxy-4-(phenylseleno)-1-cyclohexene-1-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:

: 645-96-5
Benzeneselenol

: 76985-85-8
methyl (1α,6α)-2β-hydroxy-7-oxabicyclo<4.1.0>hept-3-ene-4-carboxylate

: 119999-59-6,135358-01-9
(3S,4S,5S)-5-Bromo-3,4-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester

: 119999-50-7,120056-38-4
(3S,4S,5R)-3,5-Dihydroxy-4-phenylselanyl-cyclohex-1-enecarboxylic acid methyl ester

: 119999-51-8,120056-35-1
Methyl (3α,4α,5β)-3,4-dihydroxy-5-(phenylseleno)-1-cyclohexene-1-carboxylate

Guidance literature:: With n-butyllithium; zinc dibromide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, hexane, 0-5 deg C; 2.) room temp., 21 h;
DOI:10.1021/ja00191a040

Reference yield:

: 119999-50-7
(-)-Methyl (3α,4β,5α)-3,5-dihydroxy-4-(phenylseleno)-1-cyclohexene-1-carboxylate

: 532-32-1
sodium benzoate

Guidance literature:: Multi-step reaction with 9 steps

1: n-Bu₃SnH, AIBN / benzene / 12 h / Heating

2: Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature

3: DMAP / CH₂Cl₂ / 4 h / Ambient temperature

4: NaOCH₃ / methanol / 0.67 h / 0 - 5 °C

5: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) room temp., 13 h

6: 75 percent / n-Bu₄NIO₄, Na₂HPO₄ / CDCl₃ / 1.75 h / Ambient temperature

7: Rh₂(OAc)4 / benzene / 3 h / 75 °C

8: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, hexane, -78 deg C, 10 min; 2.) -78 deg C, 20 min

9: NaOH / tetrahydrofuran; H₂O / 0.83 h / 0 °C

With dmap; dirhodium tetraacetate; sodium hydroxide; disodium hydrogenphosphate; n-butyllithium; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; sodium methylate; tetrabutylammonium periodite; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; chloroform-d1; dichloromethane; water; benzene;
DOI:10.1021/ja00191a040

Reference yield:

: 119999-50-7
(-)-Methyl (3α,4β,5α)-3,5-dihydroxy-4-(phenylseleno)-1-cyclohexene-1-carboxylate

: 19438-10-9
methyl 3-hydroxybenzoate

Guidance literature:: Multi-step reaction with 6 steps

1: n-Bu₃SnH, AIBN / benzene / 12 h / Heating

2: Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature

3: DMAP / CH₂Cl₂ / 4 h / Ambient temperature

4: NaOCH₃ / methanol / 0.67 h / 0 - 5 °C

5: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) room temp., 13 h

6: 6 percent / n-Bu₄NIO₄, Na₂HPO₄ / CDCl₃ / 1.75 h / Ambient temperature

With dmap; disodium hydrogenphosphate; n-butyllithium; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; sodium methylate; tetrabutylammonium periodite; triphenylphosphine; In tetrahydrofuran; methanol; chloroform-d1; dichloromethane; benzene;
DOI:10.1021/ja00191a040