Benzoic acid (2E,4E)-(S)-1-((R)-2-{(2S,3R,5S)-2-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-1-methyl-ethyl)-5-((4R,5R)-4-ethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-4-methyl-penta-2,4-dienyl ester

Base Information

• Chemical Name: Benzoic acid (2E,4E)-(S)-1-((R)-2-{(2S,3R,5S)-2-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-1-methyl-ethyl)-5-((4R,5R)-4-ethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-4-methyl-penta-2,4-dienyl ester
• CAS No.: 83076-39-5
• Molecular Formula: C₄₈H₆₆O₇Si
• Molecular Weight: 783.133
• Mol file: 83076-39-5.mol

Synonyms:Benzoic acid (2E,4E)-(S)-1-((R)-2-{(2S,3R,5S)-2-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-1-methyl-ethyl)-5-((4R,5R)-4-ethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-4-methyl-penta-2,4-dienyl ester

Chemical Property of Benzoic acid (2E,4E)-(S)-1-((R)-2-{(2S,3R,5S)-2-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-1-methyl-ethyl)-5-((4R,5R)-4-ethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-4-methyl-penta-2,4-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2E,4E)-(S)-1-((R)-2-{(2S,3R,5S)-2-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-1-methyl-ethyl)-5-((4R,5R)-4-ethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-4-methyl-penta-2,4-dienyl ester

There total 10 articles about Benzoic acid (2E,4E)-(S)-1-((R)-2-{(2S,3R,5S)-2-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-1-methyl-ethyl)-5-((4R,5R)-4-ethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-4-methyl-penta-2,4-dienyl 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:

(1S,2S,3R)-3-(2-Benzyloxy-ethyl)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentanol (83061-03-4) → Benzoic acid (2E,4E)-(S)-1-((R)-2-{(2S,3R,5S)-2-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-1-methyl-ethyl)-5-((4R,5R)-4-ethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-4-methyl-penta-2,4-dienyl ester (83076-39-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) CrO₃*2Py, 2.) MCPBA, NaHCO₃, <(Me)3CC₆H₂(Me)OH>2S / 1.) CH₂Cl₂, 0 deg C (10 min) -> 25 deg C (30 min), 2.) 0 deg C

2: LDA / tetrahydrofuran / -78 deg C -> -40 deg C

3: hydrogen / Pd-C / ethanol

4: CrO₃*2Py / CH₂Cl₂

5: TsOH

6: 95 percent / LiAlH₄ / diethyl ether / 0 °C

7: 95 percent / CrO₃*2Py / CH₂Cl₂ / 1 h / 0 °C

9: LiAlH₄ / tetrahydrofuran / 5 °C

10: DMAP, Py

With pyridine; dmap; lithium aluminium tetrahydride; <(Me)3CC6H2(Me)OH>2S; hydrogen; dipyridine chromium trioxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ja00385a038

Reference yield:

(5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-pyran-2-one (83061-04-5) → Benzoic acid (2E,4E)-(S)-1-((R)-2-{(2S,3R,5S)-2-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-1-methyl-ethyl)-5-((4R,5R)-4-ethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-4-methyl-penta-2,4-dienyl ester (83076-39-5)

Guidance literature:

Multi-step reaction with 9 steps

1: LDA / tetrahydrofuran / -78 deg C -> -40 deg C

2: hydrogen / Pd-C / ethanol

3: CrO₃*2Py / CH₂Cl₂

4: TsOH

5: 95 percent / LiAlH₄ / diethyl ether / 0 °C

6: 95 percent / CrO₃*2Py / CH₂Cl₂ / 1 h / 0 °C

8: LiAlH₄ / tetrahydrofuran / 5 °C

9: DMAP, Py

With pyridine; dmap; lithium aluminium tetrahydride; hydrogen; dipyridine chromium trioxide; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ja00385a038

Reference yield:

(5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-tetrahydro-pyran-2-one → Benzoic acid (2E,4E)-(S)-1-((R)-2-{(2S,3R,5S)-2-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-1-methyl-ethyl)-5-((4R,5R)-4-ethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-4-methyl-penta-2,4-dienyl ester (83076-39-5)

Guidance literature:

Multi-step reaction with 8 steps

1: hydrogen / Pd-C / ethanol

2: CrO₃*2Py / CH₂Cl₂

3: TsOH

4: 95 percent / LiAlH₄ / diethyl ether / 0 °C

5: 95 percent / CrO₃*2Py / CH₂Cl₂ / 1 h / 0 °C

7: LiAlH₄ / tetrahydrofuran / 5 °C

8: DMAP, Py

With pyridine; dmap; lithium aluminium tetrahydride; hydrogen; dipyridine chromium trioxide; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ja00385a038

upstream raw materials:

benzoyl chloride

(R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propan-1-ol

(R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionaldehyde

(1S,2S,3R)-3-(2-Benzyloxy-ethyl)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentanol

Downstream raw materials:

(+)-tylonolide hemiacetal

(3S,4S)-4-[(2S,3R,5S)-3-((4E,6E)-(2R,3S,8R,9R)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanoic acid methyl ester

C₅₈H₆₆O₁₀

(3R,4S)-4-[(2S,3R,5S)-3-((4E,6E)-(2R,3S,8R,9R)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanethioic acid S-pyridin-2-yl ester