(2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-decahydro-1,5-dioxa-benzocyclooctene

Base Information

• Chemical Name: (2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-decahydro-1,5-dioxa-benzocyclooctene
• CAS No.: 193279-76-4
• Molecular Formula: C₄₂H₅₂O₇
• Molecular Weight: 668.871

Synonyms:(2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-decahydro-1,5-dioxa-benzocyclooctene

Chemical Property of (2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-decahydro-1,5-dioxa-benzocyclooctene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-decahydro-1,5-dioxa-benzocyclooctene

There total 27 articles about (2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-decahydro-1,5-dioxa-benzocyclooctene 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:

{(4aS,6R,7S,9S,10aR)-6-[4-(2-Ethoxy-ethoxy)-but-2-ynyl]-2,2,9-trimethyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-yloxy}-triisopropyl-silane (1054689-67-6) → (2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-decahydro-1,5-dioxa-benzocyclooctene (193279-76-4)

Guidance literature:

Multi-step reaction with 20 steps

1: PPTS / propan-1-ol

2: Red-Al / diethyl ether

3: 97 percent / (D)-(-)-diethyl tartrate, Ti(O(i-Pr))4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / -20 °C

4: SO₃-pyridine, Et₃N, DMSO / 1,2-dichloro-ethane

5: toluene

6: Bu₄NF / tetrahydrofuran

7: Pd(PPh₃)4, PPh₃ / CH₂Cl₂ / 0.08 h

8: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

9: 92 percent / NaH / dimethylformamide; tetrahydrofuran / 0 °C

10: p-MeC₆H₄SO₃H*H₂O / methanol

11: PPTS / 1,2-dichloro-ethane

12: 97 percent / DIBAL-H / CH₂Cl₂ / -40 °C

13: Et₃N / CH₂Cl₂ / 0 °C

14: 94 percent / 18-crown-6 / dimethylformamide / 50 °C

15: DIBAL-H / CH₂Cl₂ / -60 °C

16: toluene

17: DIBAL-H / CH₂Cl₂ / -78 °C

18: 90 percent / (D)-(-)-diethyl tartrate, Ti(O(i-Pr))4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / -20 °C

19: SO₃-pyridine, Et₃N, DMSO / 1,2-dichloro-ethane

20: NaN(SiMe₃)2 / tetrahydrofuran / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; methanol; propan-1-ol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/a702158e

Reference yield:

((4aS,6R,7S,9S,10aR)-6-Benzyloxymethoxymethyl-2,2,9-trimethyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-yloxy)-triisopropyl-silane (193279-67-3) → (2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-decahydro-1,5-dioxa-benzocyclooctene (193279-76-4)

Guidance literature:

Multi-step reaction with 23 steps

1: 87 percent / H₂ / Pd(OH)2/C / ethyl acetate

2: Et₃N / 1,2-dichloro-ethane / -15 °C

3: BuLi / tetrahydrofuran; various solvent(s) / -78 °C

4: PPTS / propan-1-ol

5: Red-Al / diethyl ether

6: 97 percent / (D)-(-)-diethyl tartrate, Ti(O(i-Pr))4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / -20 °C

7: SO₃-pyridine, Et₃N, DMSO / 1,2-dichloro-ethane

8: toluene

9: Bu₄NF / tetrahydrofuran

10: Pd(PPh₃)4, PPh₃ / CH₂Cl₂ / 0.08 h

11: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

12: 92 percent / NaH / dimethylformamide; tetrahydrofuran / 0 °C

13: p-MeC₆H₄SO₃H*H₂O / methanol

14: PPTS / 1,2-dichloro-ethane

15: 97 percent / DIBAL-H / CH₂Cl₂ / -40 °C

16: Et₃N / CH₂Cl₂ / 0 °C

17: 94 percent / 18-crown-6 / dimethylformamide / 50 °C

18: DIBAL-H / CH₂Cl₂ / -60 °C

19: toluene

20: DIBAL-H / CH₂Cl₂ / -78 °C

21: 90 percent / (D)-(-)-diethyl tartrate, Ti(O(i-Pr))4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / -20 °C

22: SO₃-pyridine, Et₃N, DMSO / 1,2-dichloro-ethane

23: NaN(SiMe₃)2 / tetrahydrofuran / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; 18-crown-6 ether; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; methanol; propan-1-ol; diethyl ether; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/a702158e

Reference yield:

C34H38O9 (193279-78-6) → (2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-decahydro-1,5-dioxa-benzocyclooctene (193279-76-4)

Guidance literature:

Multi-step reaction with 26 steps

1: 99 percent / K₂CO₃ / methanol

2: 85 percent / PPTS / acetonitrile

3: 2,6-lutidine / 1,2-dichloro-ethane / -30 °C

4: 87 percent / H₂ / Pd(OH)2/C / ethyl acetate

5: Et₃N / 1,2-dichloro-ethane / -15 °C

6: BuLi / tetrahydrofuran; various solvent(s) / -78 °C

7: PPTS / propan-1-ol

8: Red-Al / diethyl ether

9: 97 percent / (D)-(-)-diethyl tartrate, Ti(O(i-Pr))4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / -20 °C

10: SO₃-pyridine, Et₃N, DMSO / 1,2-dichloro-ethane

11: toluene

12: Bu₄NF / tetrahydrofuran

13: Pd(PPh₃)4, PPh₃ / CH₂Cl₂ / 0.08 h

14: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

15: 92 percent / NaH / dimethylformamide; tetrahydrofuran / 0 °C

16: p-MeC₆H₄SO₃H*H₂O / methanol

17: PPTS / 1,2-dichloro-ethane

18: 97 percent / DIBAL-H / CH₂Cl₂ / -40 °C

19: Et₃N / CH₂Cl₂ / 0 °C

20: 94 percent / 18-crown-6 / dimethylformamide / 50 °C

21: DIBAL-H / CH₂Cl₂ / -60 °C

22: toluene

23: DIBAL-H / CH₂Cl₂ / -78 °C

24: 90 percent / (D)-(-)-diethyl tartrate, Ti(O(i-Pr))4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / -20 °C

25: SO₃-pyridine, Et₃N, DMSO / 1,2-dichloro-ethane

26: NaN(SiMe₃)2 / tetrahydrofuran / 0 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; 18-crown-6 ether; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; methanol; propan-1-ol; diethyl ether; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/a702158e

upstream raw materials:

Methyltriphenylphosphonium bromide

{(4aS,6R,7S,9S,10aR)-6-[4-(2-Ethoxy-ethoxy)-but-2-ynyl]-2,2,9-trimethyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-yloxy}-triisopropyl-silane

((4aS,6R,7S,9S,10aR)-6-Benzyloxymethoxymethyl-2,2,9-trimethyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-yloxy)-triisopropyl-silane

(E)-3-[(2R,3R)-3-((4aS,6R,7S,9S,10aR)-2,2,9-Trimethyl-7-triisopropylsilanyloxy-hexahydro-1,3,5-trioxa-benzocycloocten-6-ylmethyl)-oxiranyl]-acrylic acid methyl ester

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