(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

Base Information

Chemical Name:(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
CAS No.:216493-97-9
Molecular Formula:C₂₅H₃₉IO₅
Molecular Weight:546.486
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 24 articles about (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 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: 94.0%

: 216493-92-4
(2R,3S,4S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-7-triisopropylsilanyloxy-heptanoic acid (E)-(1R,2R)-1-ethyl-4-iodo-2-methyl-but-3-enyl ester

: 216493-97-9
(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

Guidance literature:: With hydrogen fluoride; In acetonitrile; Ambient temperature;
DOI:10.1021/jo9809433

Reference yield:

: 108393-28-8
(2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol

: 216493-97-9
(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

Guidance literature:: Multi-step reaction with 12 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

With 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; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/jo9809433

Reference yield:

: 183293-40-5
(2S,3S,4S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentan-3-ol

: 216493-97-9
(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

Guidance literature:: Multi-step reaction with 11 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

With 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; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/jo9809433