6-Hepten-2-one, 3,5-dimethoxy-4-methyl-7-phenyl-, (3R,4R,5S,6E)-

Base Information

• Chemical Name: 6-Hepten-2-one, 3,5-dimethoxy-4-methyl-7-phenyl-, (3R,4R,5S,6E)-
• CAS No.: 602277-11-2
• Molecular Formula: C16H22O3
• Molecular Weight: 262.349

Synonyms:

Chemical Property of 6-Hepten-2-one, 3,5-dimethoxy-4-methyl-7-phenyl-, (3R,4R,5S,6E)-

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 6-Hepten-2-one, 3,5-dimethoxy-4-methyl-7-phenyl-, (3R,4R,5S,6E)-

There total 15 articles about 6-Hepten-2-one, 3,5-dimethoxy-4-methyl-7-phenyl-, (3R,4R,5S,6E)- 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: 91.0%

(E)-(3R,4R,5S)-3,5-Dimethoxy-4-methyl-7-phenyl-hept-6-en-2-ol (602277-10-1) → (E)-(3R,4R,5S)-3,5-Dimethoxy-4-methyl-7-phenyl-hept-6-en-2-one (602277-11-2)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(03)01256-5

Reference yield:

1,2:5,6-di-O-cyclohexylidene-α-D-ribo-3-hexofuranose-3-ulose (18546-21-9) → (E)-(3R,4R,5S)-3,5-Dimethoxy-4-methyl-7-phenyl-hept-6-en-2-one (602277-11-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 67 percent / tetrahydrofuran / 0.5 h / -10 °C

2.1: 97 percent / H₂ / Pd/C / 3 h / 2585.74 Torr

3.1: 83 percent / aq. H₂SO₄ / methanol / 24 h

4.1: MsCl; NEt₃ / CH₂Cl₂ / 2 h / 0 - 20 °C

4.2: EtCOMe; NaI / CH₂Cl₂ / 6 h / Heating

5.1: 63 percent / PPh₃; NEt₃; TBAI / Pd(OAc)2 / dimethylformamide / 6 h / 110 °C

6.1: 82 percent / Amberlyst IR-120 (H+) resin / methanol / 8 h / Heating

7.1: 95 percent / NaH / tetrahydrofuran / 3 h / 20 °C

8.1: 79 percent / H₂SO₄; aq. acetic acid / 6 h / 80 °C

9.1: 75 percent / tetrahydrofuran / 2.5 h / 20 °C

10.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

11.1: DEAD; TPP; 4-nitrobenzoic acid / tetrahydrofuran / 5 h / 20 °C

11.2: LiOH / methanol / 62 h / 20 °C

12.1: 96 percent / KH / tetrahydrofuran / 3.5 h / 20 °C

13.1: 93 percent / TBAF / tetrahydrofuran / 36 h / 20 °C

14.1: 91 percent / Dess-Martin-periodinane / CH₂Cl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; Amberlyst IR-120 (H+) resin; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; thiamine diphosphate; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; Dess-Martin periodane; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Wittig reaction / 5.1: Heck reaction / 11.1: Mitsunobu reaction;

DOI:10.1016/S0040-4039(03)01256-5

Reference yield:

1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose (23397-76-4) → (E)-(3R,4R,5S)-3,5-Dimethoxy-4-methyl-7-phenyl-hept-6-en-2-one (602277-11-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 78 percent / PDC; 4 Angstroem MS; Ac₂O / CH₂Cl₂ / 12 h / 20 °C

2.1: 67 percent / tetrahydrofuran / 0.5 h / -10 °C

3.1: 97 percent / H₂ / Pd/C / 3 h / 2585.74 Torr

4.1: 83 percent / aq. H₂SO₄ / methanol / 24 h

5.1: MsCl; NEt₃ / CH₂Cl₂ / 2 h / 0 - 20 °C

5.2: EtCOMe; NaI / CH₂Cl₂ / 6 h / Heating

6.1: 63 percent / PPh₃; NEt₃; TBAI / Pd(OAc)2 / dimethylformamide / 6 h / 110 °C

7.1: 82 percent / Amberlyst IR-120 (H+) resin / methanol / 8 h / Heating

8.1: 95 percent / NaH / tetrahydrofuran / 3 h / 20 °C

9.1: 79 percent / H₂SO₄; aq. acetic acid / 6 h / 80 °C

10.1: 75 percent / tetrahydrofuran / 2.5 h / 20 °C

11.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

12.1: DEAD; TPP; 4-nitrobenzoic acid / tetrahydrofuran / 5 h / 20 °C

12.2: LiOH / methanol / 62 h / 20 °C

13.1: 96 percent / KH / tetrahydrofuran / 3.5 h / 20 °C

14.1: 93 percent / TBAF / tetrahydrofuran / 36 h / 20 °C

15.1: 91 percent / Dess-Martin-periodinane / CH₂Cl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; dipyridinium dichromate; 4 Angstroem MS; Amberlyst IR-120 (H+) resin; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; thiamine diphosphate; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; Dess-Martin periodane; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Wittig reaction / 6.1: Heck reaction / 12.1: Mitsunobu reaction;

DOI:10.1016/S0040-4039(03)01256-5

upstream raw materials:

(E)-(3R,4R,5S)-3,5-Dimethoxy-4-methyl-7-phenyl-hept-6-en-2-ol

1,2:5,6-di-O-cyclohexylidene-α-D-ribo-3-hexofuranose-3-ulose

1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose

(3R,4R,5R)-3-Methoxy-4-methyl-5-((E)-styryl)-tetrahydro-furan-2-ol

Downstream raw materials:

((E)-(3S,4R,5R)-3,5-Dimethoxy-4,6-dimethyl-hepta-1,6-dienyl)-benzene

3,5-dimethoxy-2,4-dimethyl-7-phenyl-(2S,3S,4R,5S,6E)-6-hepten-1-ol

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