(4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one

Base Information

• Chemical Name: (4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one
• CAS No.: 139403-50-2
• Molecular Formula: C₁₄H₁₈O₂Se
• Molecular Weight: 297.256

Synonyms:(4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one

Chemical Property of (4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one

Chemical Property:

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Technology Process of (4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one

There total 28 articles about (4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-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: 89.0%

bis(phenylseleno)methane (20343-90-2) + (+/-)-cis-5,6-dimethyl-5,6-dihydro-2H-pyran-2-one (71816-81-4,104486-83-1,111266-07-0,118574-92-8) → (4S*,5R*,6R*)-5,6-dimethyl-4-phenylselenomethyltetrahydro-2H-pyran-2-one (111194-12-8,130605-68-4,139403-50-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -85 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)81980-3

Reference yield: 72.0%

(3S,4R,5R)-5-(4-Chlorobenzoyloxy)-4-methyl-3-(phenylselanylmethyl)hexanoic acid (210691-73-9) → (4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one (139403-50-2)

Guidance literature:

(3S,4R,5R)-5-(4-Chlorobenzoyloxy)-4-methyl-3-(phenylselanylmethyl)hexanoic acid; With n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; at -78 - -20 ℃; for 3.08333h;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; dichloromethane; for 24h;

DOI:10.1039/a909898d

Reference yield: 59.0%

(+/-)-cis-5,6-dimethyl-5,6-dihydro-2H-pyran-2-one (71816-81-4,104486-83-1,111266-07-0,118574-92-8) + lithio-phenylselenyl-methane (22859-62-7) → (4S*,5R*,6R*)-5,6-dimethyl-4-phenylselenomethyltetrahydro-2H-pyran-2-one (111194-12-8,130605-68-4,139403-50-2)

Guidance literature:

In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -85 ℃; for 1h;

DOI:10.1039/c39870000106

upstream raw materials:

bis(phenylseleno)methane

(+/-)-cis-5,6-dimethyl-5,6-dihydro-2H-pyran-2-one

lithio-phenylselenyl-methane

(2R*,3R*)-3-methyl-4-pentyne-2-ol

Downstream raw materials:

((4S,5R,6R)-2-Hydroxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-(1-methoxy-1-methyl-ethoxy)-acetic acid 2-trimethylsilanyl-ethyl ester

N-{(S)-[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-2,3-dimethoxy-propyl)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methoxy-methyl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide

N-{(S)-[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-2,3-dimethoxy-propyl)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methoxy-methyl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-hydroxy-acetamide

N-{(S)-[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-2,3-dimethoxy-propyl)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methoxy-methyl}-2-hydroxy-2-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-acetamide

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