(E)-3-[(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]-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-[(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]-acrylic acid ethyl ester
• CAS No.: 182617-16-9
• Molecular Formula: C₃₉H₅₆O₉
• Molecular Weight: 668.868

Synonyms:(E)-3-[(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]-acrylic acid ethyl ester

Chemical Property of (E)-3-[(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]-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(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]-acrylic acid ethyl ester

There total 27 articles about (E)-3-[(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]-acrylic 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:

p-methoxybenzyl chloride (824-94-2) → (E)-3-[(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]-acrylic acid ethyl ester (182617-16-9)

Guidance literature:

Multi-step reaction with 26 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

22: 88 percent / CSA / CH₂Cl₂ / Ambient temperature

23: 93 percent / DIBAH / toluene / -78 °C

24: 76 percent / t-BuOOH, L-(+)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

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

26: NaH / tetrahydrofuran / 0 deg C to RT

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; camphor-10-sulfonic acid; 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)-3-[(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]-acrylic acid ethyl ester (182617-16-9)

Guidance literature:

Multi-step reaction with 26 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

22: 88 percent / CSA / CH₂Cl₂ / Ambient temperature

23: 93 percent / DIBAH / toluene / -78 °C

24: 76 percent / t-BuOOH, L-(+)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

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

26: NaH / tetrahydrofuran / 0 deg C to RT

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; camphor-10-sulfonic acid; 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:

(E)-(R)-7-Benzyloxy-5-(4-methoxy-benzyloxy)-2-methyl-hept-2-en-1-ol (182617-04-5) → (E)-3-[(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]-acrylic acid ethyl ester (182617-16-9)

Guidance literature:

Multi-step reaction with 22 steps

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

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

3: NaH / tetrahydrofuran / 0 deg C to RT

4: 96 percent / Pd₂(dba)3*CHCl₃, n-Bu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

5: 100 percent / Ag₂O / acetonitrile / 85 °C

6: 83 percent / DIBAH / toluene / -78 °C

7: 87 percent / t-BuOOH, D-(-)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

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

9: toluene / 120 °C

10: 99 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

11: 95 percent / imidazole / dimethylformamide / Ambient temperature

12: 80 percent / DIBAH / toluene / -78 °C

13: 78 percent / t-BuOOH, D-(-)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

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

15: n-BuLi / tetrahydrofuran / 0 °C

16: 72 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

17: 75 percent / AcOH / H₂O / Ambient temperature

18: 88 percent / CSA / CH₂Cl₂ / Ambient temperature

19: 93 percent / DIBAH / toluene / -78 °C

20: 76 percent / t-BuOOH, L-(+)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

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

22: NaH / tetrahydrofuran / 0 deg C to RT

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; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

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

upstream raw materials:

diethoxyphosphoryl-acetic 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:

(2R,3S,4S)-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}-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal

(E)-(4S,5R,6S)-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-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hept-2-enoic acid ethyl ester

(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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