(4aR,6R,7aS,9R,10R,11aR,12aS)-10-Benzyloxy-9-((E)-3-benzyloxy-propenyl)-3-(4-methoxy-phenyl)-6-methyl-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cyclooctene

Base Information

• Chemical Name: (4aR,6R,7aS,9R,10R,11aR,12aS)-10-Benzyloxy-9-((E)-3-benzyloxy-propenyl)-3-(4-methoxy-phenyl)-6-methyl-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cyclooctene
• CAS No.: 193279-73-1
• Molecular Formula: C₃₇H₄₄O₇
• Molecular Weight: 600.752

Synonyms:(4aR,6R,7aS,9R,10R,11aR,12aS)-10-Benzyloxy-9-((E)-3-benzyloxy-propenyl)-3-(4-methoxy-phenyl)-6-methyl-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cyclooctene

Chemical Property of (4aR,6R,7aS,9R,10R,11aR,12aS)-10-Benzyloxy-9-((E)-3-benzyloxy-propenyl)-3-(4-methoxy-phenyl)-6-methyl-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cyclooctene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,7aS,9R,10R,11aR,12aS)-10-Benzyloxy-9-((E)-3-benzyloxy-propenyl)-3-(4-methoxy-phenyl)-6-methyl-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cyclooctene

There total 18 articles about (4aR,6R,7aS,9R,10R,11aR,12aS)-10-Benzyloxy-9-((E)-3-benzyloxy-propenyl)-3-(4-methoxy-phenyl)-6-methyl-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cyclooctene 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-Benzyloxymethoxymethyl-2,2,9-trimethyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-yloxy)-triisopropyl-silane (193279-67-3) → (4aR,6R,7aS,9R,10R,11aR,12aS)-10-Benzyloxy-9-((E)-3-benzyloxy-propenyl)-3-(4-methoxy-phenyl)-6-methyl-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cyclooctene (193279-73-1)

Guidance literature:

Multi-step reaction with 14 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; 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:

{(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) → (4aR,6R,7aS,9R,10R,11aR,12aS)-10-Benzyloxy-9-((E)-3-benzyloxy-propenyl)-3-(4-methoxy-phenyl)-6-methyl-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cyclooctene (193279-73-1)

Guidance literature:

Multi-step reaction with 11 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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:

(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 (193279-71-9) → (4aR,6R,7aS,9R,10R,11aR,12aS)-10-Benzyloxy-9-((E)-3-benzyloxy-propenyl)-3-(4-methoxy-phenyl)-6-methyl-decahydro-2,4,8,12-tetraoxa-dibenzo[a,d]cyclooctene (193279-73-1)

Guidance literature:

Multi-step reaction with 6 steps

1: Bu₄NF / tetrahydrofuran

2: Pd(PPh₃)4, PPh₃ / CH₂Cl₂ / 0.08 h

3: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

4: 92 percent / NaH / dimethylformamide; tetrahydrofuran / 0 °C

5: p-MeC₆H₄SO₃H*H₂O / methanol

6: PPTS / 1,2-dichloro-ethane

With tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1039/a702158e

upstream raw materials:

p-Anisaldehyde dimethyl acetal

{(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

Downstream raw materials:

[(2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile

(E)-4-[(2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-decahydro-1,5-dioxa-benzocycloocten-6-yl]-2-methyl-but-2-en-1-ol

{(2R,3R)-3-[(2R,3R,4aR,6S,7R,9S,10aS)-3-Benzyloxy-2-((E)-3-benzyloxy-propenyl)-7-(4-methoxy-benzyloxy)-9-methyl-decahydro-1,5-dioxa-benzocycloocten-6-ylmethyl]-2-methyl-oxiranyl}-methanol

(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

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