Mosher Ester Derivative of (3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-7-(hydroxymethyl)-2,2-dimethyl-1H-cyclopentapentalene

Base Information

• Chemical Name: Mosher Ester Derivative of (3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-7-(hydroxymethyl)-2,2-dimethyl-1H-cyclopenta
• Molecular Formula: C₂₄H₂₉F₃O₃
• Molecular Weight: 422.488

Synonyms:Mosher Ester Derivative of (3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-7-(hydroxymethyl)-2,2-dimethyl-1H-cyclopentapentalene

Chemical Property of Mosher Ester Derivative of (3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-7-(hydroxymethyl)-2,2-dimethyl-1H-cyclopenta

Chemical Property:

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There total 9 articles about Mosher Ester Derivative of (3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-7-(hydroxymethyl)-2,2-dimethyl-1H-cyclopentapentalene 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: 90.0%

(S)-Mosher acid (17257-71-5,20445-31-2,56135-03-6,81655-41-6) + (3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-7-(hydroxymethyl)-2,2-dimethyl-1H-cyclopentapentalene (77837-17-3,82310-23-4) → Mosher Ester Derivative of (3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-7-(hydroxymethyl)-2,2-dimethyl-1H-cyclopentapentalene (87726-10-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 16h; 0 deg C to RT;

DOI:10.1021/jo00172a009

Reference yield:

2-hydroxy-4,4-dimethyltetrahydropyran (72603-19-1) → Mosher Ester Derivative of (3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-7-(hydroxymethyl)-2,2-dimethyl-1H-cyclopentapentalene (87726-10-1)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH / 1.) acetonitrile, RT, 2 h, 2.) reflux, 20 h

2: 69 percent / pyridinium dichromate / CH₂Cl₂ / 5 h / Ambient temperature

3: 97 percent / diethylamine / methanol / 1.5 h / 0 deg C to RT

5: 1.) Zn/Cu, 2.) potassium ferricyanide / 1.) MeOH, RT, 45 min, 2.) H₂O, 0 deg C, 15 min

6: acetonitrile / 5 h / Heating

7: 97 percent / LiAlH₄ / diethyl ether / 0.75 h / Ambient temperature

8: 90 percent / DMAP, DCC / CH₂Cl₂ / 16 h / 0 deg C to RT

With dmap; lithium aluminium tetrahydride; dipyridinium dichromate; copper; sodium hydride; diethylamine; dicyclohexyl-carbodiimide; potassium hexacyanoferrate(III); zinc; In methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jo00172a009

Reference yield:

(l)-(-)-Menthyl (E)-7-Oxo-5,5-dimethylhept-2-enoate (87655-95-6) → Mosher Ester Derivative of (3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-7-(hydroxymethyl)-2,2-dimethyl-1H-cyclopentapentalene (87726-10-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / diethylamine / methanol / 1.5 h / 0 deg C to RT

3: 1.) Zn/Cu, 2.) potassium ferricyanide / 1.) MeOH, RT, 45 min, 2.) H₂O, 0 deg C, 15 min

4: acetonitrile / 5 h / Heating

5: 97 percent / LiAlH₄ / diethyl ether / 0.75 h / Ambient temperature

6: 90 percent / DMAP, DCC / CH₂Cl₂ / 16 h / 0 deg C to RT

With dmap; lithium aluminium tetrahydride; copper; diethylamine; dicyclohexyl-carbodiimide; potassium hexacyanoferrate(III); zinc; In methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jo00172a009

upstream raw materials:

(S)-Mosher acid

(3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-7-(hydroxymethyl)-2,2-dimethyl-1H-cyclopentapentalene

2-hydroxy-4,4-dimethyltetrahydropyran

(l)-(-)-Menthyl (E)-7-Oxo-5,5-dimethylhept-2-enoate

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