(3aS,6S,7aR)-α³-<(benzyloxy)methoxy>-2-hydroxy-α⁴-methylcyclohexane-1,4-diacetic acid γ-lactone

Base Information

• Chemical Name: (3aS,6S,7aR)-α³-<(benzyloxy)methoxy>-2-hydroxy-α⁴-methylcyclohexane-1,4-diacetic acid γ-lactone
• CAS No.: 82167-76-8
• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.396

Synonyms:(3aS,6S,7aR)-α³-<(benzyloxy)methoxy>-2-hydroxy-α⁴-methylcyclohexane-1,4-diacetic acid γ-lactone

Chemical Property of (3aS,6S,7aR)-α³-<(benzyloxy)methoxy>-2-hydroxy-α⁴-methylcyclohexane-1,4-diacetic acid γ-lactone

Chemical Property:

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Technology Process of (3aS,6S,7aR)-α³-<(benzyloxy)methoxy>-2-hydroxy-α⁴-methylcyclohexane-1,4-diacetic acid γ-lactone

There total 9 articles about (3aS,6S,7aR)-α³-<(benzyloxy)methoxy>-2-hydroxy-α⁴-methylcyclohexane-1,4-diacetic acid γ-lactone 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:

(3aS,6S,7aR)-3-<(benzyloxy)methoxy>hexahydro-6-(2-hydroxy-1-methylethyl)-2(3H)-benzofuranone (82167-75-7) → (3aS,6S,7aR)-α3-<(benzyloxy)methoxy>-2-hydroxy-α4-methylcyclohexane-1,4-diacetic acid γ-lactone (82167-76-8)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 0.5h;

DOI:10.1021/jo00179a018

Reference yield:

(1S,2S,4S)-7-<(benzyloxy)methoxy>-2,9-dihydroxy-p-methane-7-carbonitrile (88670-93-3) → (3aS,6S,7aR)-α3-<(benzyloxy)methoxy>-2-hydroxy-α4-methylcyclohexane-1,4-diacetic acid γ-lactone (82167-76-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / KOH / ethanol / 100 °C

2: PPh₃, EtOOCN=NCOOEt / tetrahydrofuran / -20 °C

3: Jones reagent / acetone / 0 °C

With potassium hydroxide; jones reagent; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; acetone;

DOI:10.1021/ja00380a035

Reference yield:

(4S)-7-<(benzyloxy)methoxy>-p-mentha-1,8-diene-7-carbonitrile (82167-73-5) → (3aS,6S,7aR)-α3-<(benzyloxy)methoxy>-2-hydroxy-α4-methylcyclohexane-1,4-diacetic acid γ-lactone (82167-76-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) thexylborane, 2.) H₂O, NaOAc / 1) THF, -40 deg C

2: 95 percent / KOH / ethanol / 100 °C

3: PPh₃, EtOOCN=NCOOEt / tetrahydrofuran / -20 °C

4: Jones reagent / acetone / 0 °C

With potassium hydroxide; jones reagent; thexylborane; water; sodium acetate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; acetone;

DOI:10.1021/ja00380a035

upstream raw materials:

(3aS,6S,7aR)-3-<(benzyloxy)methoxy>hexahydro-6-(2-hydroxy-1-methylethyl)-2(3H)-benzofuranone

Benzyloxymethyl chloride

(S)-(-)-perillaldehyde

(4S)-7-<(benzyloxy)methoxy>-p-mentha-1,8-diene-7-carbonitrile

Downstream raw materials:

(3aS,6S,7aR)-3-<(benzyloxy)methoxy>hexahydro-6-vinyl-2(3H)-benzofuranone

(+)-Phyllanthocin

(3R,3aS,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>hexahydro-6-vinyl-2(3H)-benzofuranone

(3R,3aS,6S,7aR)-3-Benzyloxymethoxy-3-benzyloxymethyl-2-((S)-4-hydroxy-3-methyl-2-methylene-butyl)-6-vinyl-octahydro-benzofuran-2-ol

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