(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-enoic acid ethyl ester

Base Information

Chemical Name:(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-enoic acid ethyl ester
CAS No.:193279-87-7
Molecular Formula:C₄₃H₅₄O₈
Molecular Weight:698.897
Hs Code.:

(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-enoic acid ethyl ester

Synonyms:(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-enoic acid ethyl ester

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Chemical Property of (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-enoic acid ethyl ester

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Technology Process of (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-enoic acid ethyl ester

There total 23 articles about (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-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:

: 1054689-67-6
{(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

: 193279-87-7
(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-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 16 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; 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:

: 193279-67-3
((4aS,6R,7S,9S,10aR)-6-Benzyloxymethoxymethyl-2,2,9-trimethyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-yloxy)-triisopropyl-silane

: 193279-87-7
(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-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 19 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

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; 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:

: 193279-71-9
(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

: 193279-87-7
(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-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 11 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

7: 97 percent / DIBAL-H / CH₂Cl₂ / -40 °C

8: Et₃N / CH₂Cl₂ / 0 °C

9: 94 percent / 18-crown-6 / dimethylformamide / 50 °C

10: DIBAL-H / CH₂Cl₂ / -60 °C

11: toluene

With 18-crown-6 ether; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1039/a702158e