Benzoic acid (1R,2S)-1-[(1R,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2,3-dihydroxy-2-methyl-propyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2S)-1-[(1R,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2,3-dihydroxy-2-methyl-propyl ester
• CAS No.: 384817-54-3
• Molecular Formula: C₃₉H₅₂O₅Si
• Molecular Weight: 628.924

Synonyms:Benzoic acid (1R,2S)-1-[(1R,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2,3-dihydroxy-2-methyl-propyl ester

Chemical Property of Benzoic acid (1R,2S)-1-[(1R,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2,3-dihydroxy-2-methyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,2S)-1-[(1R,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2,3-dihydroxy-2-methyl-propyl ester

There total 7 articles about Benzoic acid (1R,2S)-1-[(1R,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2,3-dihydroxy-2-methyl-propyl 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: 66.0%

benzoic acid (65-85-0,8013-63-6) + {(2S,3S)-3-[(1R,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol (384817-52-1) → Benzoic acid (1R,2S)-1-[(1R,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2,3-dihydroxy-2-methyl-propyl ester (384817-54-3)

Guidance literature:

With titanium(IV) isopropylate; In chloroform; at 20 ℃; for 8h;

DOI:10.1016/S0040-4039(01)01608-2

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → Benzoic acid (1R,2S)-1-[(1R,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2,3-dihydroxy-2-methyl-propyl ester (384817-54-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

2: 99 percent / LiAlH₄ / diethyl ether / 0.5 h / 20 °C

3: 87 percent / TBHP; Ti(Oi-Pr)4; (+)-DET / 4 Angstroem MS / CH₂Cl₂ / 20 h / -20 °C

4: 66 percent / Ti(Oi-Pr)4 / CHCl₃ / 8 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; 4 Angstroem MS; In diethyl ether; dichloromethane; chloroform; 3: Sharpless' asymmetric epoxidation;

DOI:10.1016/S0040-4039(01)01608-2

Reference yield:

(E)-4-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-2-methyl-but-2-enoic acid (380414-34-6) → Benzoic acid (1R,2S)-1-[(1R,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2,3-dihydroxy-2-methyl-propyl ester (384817-54-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / aq. AcOH / tetrahydrofuran / 17 h / 20 °C

2: 93 percent / NaBH₄ / ethanol / 0.25 h / 20 °C

3: 86 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

4: 99 percent / LiAlH₄ / diethyl ether / 0.5 h / 20 °C

5: 87 percent / TBHP; Ti(Oi-Pr)4; (+)-DET / 4 Angstroem MS / CH₂Cl₂ / 20 h / -20 °C

6: 66 percent / Ti(Oi-Pr)4 / CHCl₃ / 8 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; acetic acid; 4 Angstroem MS; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; 5: Sharpless' asymmetric epoxidation;

DOI:10.1016/S0040-4039(01)01608-2

upstream raw materials:

benzoic acid

{(2S,3S)-3-[(1R,5R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol

tert-butylchlorodiphenylsilane

(E)-4-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-2-methyl-but-2-enoic acid

Downstream raw materials:

Benzoic acid (Z)-(1R,2S)-1-((1R,5R,6R)-6-formyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl)-4-iodo-2-methoxymethoxy-2-methyl-but-3-enyl ester

Benzoic acid (Z)-(1R,2S)-1-((1R,5R,6R)-6-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl)-4-iodo-2-methoxymethoxy-2-methyl-but-3-enyl ester

Benzoic acid (Z)-(1R,2S)-4-iodo-1-[(1R,5R,6R)-5-isopropyl-6-((E)-2-methoxycarbonyl-2-triethylsilanyloxy-vinyl)-2-methyl-cyclohex-2-enylmethyl]-2-methoxymethoxy-2-methyl-but-3-enyl ester

Benzoic acid (Z)-(1R,2S)-1-[(1R,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-4-iodo-2-methoxymethoxy-2-methyl-but-3-enyl ester

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