(2S*,3R*,4R*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran

Base Information

• Chemical Name: (2S*,3R*,4R*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran
• CAS No.: 158249-97-9
• Molecular Formula: C₃₉H₅₂O₄S
• Molecular Weight: 616.905

Synonyms:(2S*,3R*,4R*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran

Chemical Property of (2S*,3R*,4R*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran

Chemical Property:

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Technology Process of (2S*,3R*,4R*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran

There total 2 articles about (2S*,3R*,4R*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran 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:

di-L-menthyl fumarate (34675-24-6) + 1,3-diphenylprop-2-ene-1-thione (137063-57-1) → (2S*,3R*,4R*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran (158249-97-9) + (2R*,3S*,4S*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran (182266-04-2) + (2S,3R,4R)-4,6-Diphenyl-3,4-dihydro-2H-thiopyran-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Guidance literature:

With ethylaluminum dichloride; In dichloromethane; at 25 ℃; for 0.2h; Yield given. Yields of byproduct given;

DOI:10.1039/P19960001897

Reference yield:

di-L-menthyl fumarate (34675-24-6) + 1,3-diphenylprop-2-ene-1-thione (137063-57-1) → (2S*,3R*,4R*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran (158249-97-9) + (2R*,3S*,4S*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran (182266-04-2)

Guidance literature:

In chloroform; at 40 ℃; for 15h; other solvents, also Lewis acid-promoted;

Reference yield: 88.0%

(2S*,3R*,4R*)-2,3-trans-3,4-cis-2,3-Bis<(-)-menthoxycarbonyl>-3,4-diphenyl-3,4-dihydro-2H-thiopyran (158249-97-9) → (2S,3R,4R)-2,3-Bis(hydroxymethyl)-4,6-diphenyl-3,4-dihydro-2H-thiopyran (158249-98-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 3h;

DOI:10.1039/P19960001897

upstream raw materials:

di-L-menthyl fumarate

1,3-diphenylprop-2-ene-1-thione

Downstream raw materials:

(2S,3R,4R)-2,3-Bis(hydroxymethyl)-4,6-diphenyl-3,4-dihydro-2H-thiopyran

Methanesulfonic acid (2S,3R,4R)-2-methanesulfonyloxymethyl-4,6-diphenyl-3,4-dihydro-2H-thiopyran-3-ylmethyl ester

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