(2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester

Base Information

• Chemical Name: (2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester
• CAS No.: 216493-93-5
• Molecular Formula: C₂₅H₃₇IO₅
• Molecular Weight: 544.47

Synonyms:(2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester

Chemical Property of (2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester

There total 25 articles about (2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester 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:

(2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol (108393-28-8) → (2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester (216493-93-5)

Guidance literature:

Multi-step reaction with 13 steps

1: Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

2: 78 percent / H₂ / Pd/C / ethanol / 7.5 h / 2280 Torr

3: Et₃N, DMAP / CH₂Cl₂ / 3 h / 0 °C

4: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

5: tert-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

6: 94 percent / LiAlH₄ / tetrahydrofuran / 22 h / Ambient temperature

7: 98 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / Ambient temperature

8: imidazole / dimethylformamide / 24 h / Ambient temperature

9: 99 percent / DIBAL-H / toluene / 1 h / 0 °C

10: 71 percent / Jones reagent / acetone / 1 h / 0 °C

11: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1) THF, rt, 2 h; 2) benzene, rt, 24 h

12: 94 percent / aq. HF / acetonitrile / Ambient temperature

13: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 8 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; jones reagent; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; hydrogen fluoride; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1021/jo9809433

Reference yield:

(2S,3S,4S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentan-3-ol (183293-40-5) → (2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester (216493-93-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 78 percent / H₂ / Pd/C / ethanol / 7.5 h / 2280 Torr

2: Et₃N, DMAP / CH₂Cl₂ / 3 h / 0 °C

3: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

4: tert-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

5: 94 percent / LiAlH₄ / tetrahydrofuran / 22 h / Ambient temperature

6: 98 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / Ambient temperature

7: imidazole / dimethylformamide / 24 h / Ambient temperature

8: 99 percent / DIBAL-H / toluene / 1 h / 0 °C

9: 71 percent / Jones reagent / acetone / 1 h / 0 °C

10: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1) THF, rt, 2 h; 2) benzene, rt, 24 h

11: 94 percent / aq. HF / acetonitrile / Ambient temperature

12: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 8 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; jones reagent; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; hydrogen fluoride; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1021/jo9809433

Reference yield:

(4R,2'R,3'S,4'S)-4-benzyl-3-(5'-benzyloxy-3'-hydroxy-2',4'-dimethylpentanoyl)-2-oxazolidinone (183506-80-1) → (2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-oxo-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester (216493-93-5)

Guidance literature:

Multi-step reaction with 14 steps

1: LiBH₄ / tetrahydrofuran; methanol / 0.67 h / 0 °C

2: Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

3: 78 percent / H₂ / Pd/C / ethanol / 7.5 h / 2280 Torr

4: Et₃N, DMAP / CH₂Cl₂ / 3 h / 0 °C

5: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

6: tert-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

7: 94 percent / LiAlH₄ / tetrahydrofuran / 22 h / Ambient temperature

8: 98 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / Ambient temperature

9: imidazole / dimethylformamide / 24 h / Ambient temperature

10: 99 percent / DIBAL-H / toluene / 1 h / 0 °C

11: 71 percent / Jones reagent / acetone / 1 h / 0 °C

12: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1) THF, rt, 2 h; 2) benzene, rt, 24 h

13: 94 percent / aq. HF / acetonitrile / Ambient temperature

14: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 8 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; lithium borohydride; jones reagent; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; hydrogen fluoride; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1021/jo9809433

upstream raw materials:

(2R,3S,4S,6R)-7-Hydroxy-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester

p-Anisaldehyde dimethyl acetal

(2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol

(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

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