(E)-(4R,5R,7S,8S,9S,11S)-13-Benzyloxy-5,7-dihydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(4R,5R,7S,8S,9S,11S)-13-Benzyloxy-5,7-dihydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl ester
• CAS No.: 182617-24-9
• Molecular Formula: C₃₄H₅₀O₈
• Molecular Weight: 586.766

Synonyms:(E)-(4R,5R,7S,8S,9S,11S)-13-Benzyloxy-5,7-dihydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl ester

Chemical Property of (E)-(4R,5R,7S,8S,9S,11S)-13-Benzyloxy-5,7-dihydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5R,7S,8S,9S,11S)-13-Benzyloxy-5,7-dihydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl ester

There total 22 articles about (E)-(4R,5R,7S,8S,9S,11S)-13-Benzyloxy-5,7-dihydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl 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: 75.0%

(E)-(4R,5R,7S,8R,9S,11S)-13-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl ester (182617-14-7) → (E)-(4R,5R,7S,8S,9S,11S)-13-Benzyloxy-5,7-dihydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl ester (182617-24-9)

Guidance literature:

With acetic acid; In water; Ambient temperature;

DOI:10.1016/0040-4039(96)01503-1

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (E)-(4R,5R,7S,8S,9S,11S)-13-Benzyloxy-5,7-dihydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl ester (182617-24-9)

Guidance literature:

Multi-step reaction with 21 steps

1: 97 percent / NaH / dimethylformamide; tetrahydrofuran / Ambient temperature

2: MeI, NaHCO₃ / acetone; H₂O / 0 deg C to RT

3: toluene / 110 °C

4: 88 percent / DIBAH / toluene / -78 °C

5: t-BuOOH, L-(+)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

6: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C to RT

7: NaH / tetrahydrofuran / 0 deg C to RT

8: 96 percent / Pd₂(dba)3*CHCl₃, n-Bu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

9: 100 percent / Ag₂O / acetonitrile / 85 °C

10: 83 percent / DIBAH / toluene / -78 °C

11: 87 percent / t-BuOOH, D-(-)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

12: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C to RT

13: toluene / 120 °C

14: 99 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

15: 95 percent / imidazole / dimethylformamide / Ambient temperature

16: 80 percent / DIBAH / toluene / -78 °C

17: 78 percent / t-BuOOH, D-(-)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

18: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C to RT

19: n-BuLi / tetrahydrofuran / 0 °C

20: 72 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

21: 75 percent / AcOH / H₂O / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; n-butyllithium; formic acid; oxalyl dichloride; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; tributylphosphine; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; silver(l) oxide; methyl iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/0040-4039(96)01503-1

Reference yield:

(S)-4-Benzyloxy-1-[1,3]dithian-2-yl-butan-2-ol (173279-16-8) → (E)-(4R,5R,7S,8S,9S,11S)-13-Benzyloxy-5,7-dihydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl ester (182617-24-9)

Guidance literature:

Multi-step reaction with 21 steps

1: 97 percent / NaH / dimethylformamide; tetrahydrofuran / Ambient temperature

2: MeI, NaHCO₃ / acetone; H₂O / 0 deg C to RT

3: toluene / 110 °C

4: 88 percent / DIBAH / toluene / -78 °C

5: t-BuOOH, L-(+)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

6: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C to RT

7: NaH / tetrahydrofuran / 0 deg C to RT

8: 96 percent / Pd₂(dba)3*CHCl₃, n-Bu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

9: 100 percent / Ag₂O / acetonitrile / 85 °C

10: 83 percent / DIBAH / toluene / -78 °C

11: 87 percent / t-BuOOH, D-(-)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

12: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C to RT

13: toluene / 120 °C

14: 99 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

15: 95 percent / imidazole / dimethylformamide / Ambient temperature

16: 80 percent / DIBAH / toluene / -78 °C

17: 78 percent / t-BuOOH, D-(-)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

18: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C to RT

19: n-BuLi / tetrahydrofuran / 0 °C

20: 72 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

21: 75 percent / AcOH / H₂O / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; n-butyllithium; formic acid; oxalyl dichloride; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; tributylphosphine; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; silver(l) oxide; methyl iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/0040-4039(96)01503-1

upstream raw materials:

(E)-(4R,5R,7S,8R,9S,11S)-13-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,8-trimethyl-tridec-2-enoic acid ethyl ester

p-methoxybenzyl chloride

(S)-4-Benzyloxy-1-[1,3]dithian-2-yl-butan-2-ol

(E)-(R)-7-Benzyloxy-5-(4-methoxy-benzyloxy)-2-methyl-hept-2-en-1-ol

Downstream raw materials:

(E)-(R)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-pent-2-enoic acid ethyl ester

(E)-(R)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-pent-2-en-1-ol

[(2S,3S)-3-((S)-1-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2-methyl-oxiranyl]-methanol

(E)-(4S,5R,6R)-6-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-hydroxy-4-methyl-hept-2-enoic acid ethyl ester

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