tert-Butyl (5R,6S,7R,7aR)-6-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-7-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]-2-oxo-4,5,6,7-tetrahydro-2H-1-benzofuran-3-propanoate

Base Information

• Chemical Name: tert-Butyl (5R,6S,7R,7aR)-6-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-7-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]-2-oxo-4,5,6,7-tetrahydro-2H-1-benzofuran-3-propanoate
• CAS No.: 283611-59-6
• Molecular Formula: C₄₄H₆₆O₈
• Molecular Weight: 723.003
• Mol file: 283611-59-6.mol

Synonyms:tert-Butyl (5R,6S,7R,7aR)-6-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-7-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]-2-oxo-4,5,6,7-tetrahydro-2H-1-benzofuran-3-propanoate

Chemical Property of tert-Butyl (5R,6S,7R,7aR)-6-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-7-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]-2-oxo-4,5,6,7-tetrahydro-2H-1-benzofuran-3-propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl (5R,6S,7R,7aR)-6-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-7-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]-2-oxo-4,5,6,7-tetrahydro-2H-1-benzofuran-3-propanoate

There total 31 articles about tert-Butyl (5R,6S,7R,7aR)-6-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-7-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]-2-oxo-4,5,6,7-tetrahydro-2H-1-benzofuran-3-propanoate 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: 83.0%

2-(Diethoxy-phosphoryl)-pentanedioic acid 5-tert-butyl ester 1-[(1R,2R,3S,4R)-3-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-4-((E)-oct-6-enyl)-6-oxo-cyclohexyl] ester (283611-65-4) → tert-Butyl (5R,6S,7R,7aR)-6-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-7-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]-2-oxo-4,5,6,7-tetrahydro-2H-1-benzofuran-3-propanoate (283611-59-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; for 8h;

DOI:10.1135/cccc20000490

Reference yield:

pent-3-yn-1-ol (10229-10-4) → tert-Butyl (5R,6S,7R,7aR)-6-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-7-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]-2-oxo-4,5,6,7-tetrahydro-2H-1-benzofuran-3-propanoate (283611-59-6)

Guidance literature:

Multi-step reaction with 26 steps

1.1: 90 percent / pyridine / 3 h / 20 °C

2.1: CH₃Li / dioxane; diethyl ether / 0.5 h / 0 °C

2.2: dioxane / 15 h / Heating

3.1: 58 percent / TsOH / methanol / 12 h / Heating

4.1: 87 percent / Red-Al / toluene; diethyl ether / 2 h / 20 °C

5.1: 95 percent / 1,2-bis(diphenylphosphino)ethane; bromine / CH₂Cl₂ / 3 h / 20 °C

6.1: AD-mix α; NaHCO3; MeSO2NH2 / H2O; 2-methyl-propan-2-ol / 26 h / 0 °C

6.2: 74 percent / pyridinium tosylate / acetone / 35 h / 20 °C

7.1: Li / liquid ammonia / 0.17 h / -49 °C

7.2: diethyl ether; liquid ammonia / 0.75 h

8.1: diethyl ether

9.1: 79 percent / PDC; Celite / benzene; various solvent(s); diethyl ether / 8.5 h / 5 °C

10.1: tert-BuLi / diethyl ether; pentane / 2 h / -78 - -10 °C

10.2: CuCN / pentane; diethyl ether; tetrahydrofuran / 2 h / -78 - -50 °C

10.3: 91 percent / BF₃*Et₂O / tetrahydrofuran; pentane; diethyl ether / -78 - -40 °C

11.1: aq. t-BuOK / tetrahydrofuran / 4.5 h / 20 °C

12.1: 51 percent / 0.17 h / 105 °C

13.1: 46 percent / Na₂CO₃ / methanol / 13.5 h / 75 °C

14.1: 91 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.17 h / 0 °C

15.1: 89 percent / Li / liquid ammonia; tetrahydrofuran / 0.5 h

16.1: 95 percent / Hg(OCOCF₃)2; Et₃N / 20 °C

17.1: 95 percent / xylene / 5 h / 170 °C

18.1: 99 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 5 h / 20 °C

19.1: 79 percent / NIS / CH₂Cl₂ / 3 h / -70 - 20 °C

20.1: 89 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

21.1: 78 percent / CH₃I; Ag₂O / CH₂Cl₂ / 2 h

22.1: 94 percent / NaBH₄ / methanol / 0.17 h / 0 °C

23.1: 83 percent / NaH / dimethylformamide / 36 h

24.1: 53 percent / camphorsulfonic acid; Et₃N / CH₂Cl₂; dimethylsulfoxide

25.1: 81 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

26.1: 83 percent / LHMDS / tetrahydrofuran / 8 h

With pyridine; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; AD-mix-α; N-iodo-succinimide; dipyridinium dichromate; cerium(III) chloride; 2-methyl-but-2-ene; methanesulfonamide; Celite; camphor-10-sulfonic acid; potassium tert-butylate; methyllithium; bromine; tert.-butyl lithium; mercury(II) trifluoroacetate; lithium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; toluene-4-sulfonic acid; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 1,2-bis-(diphenylphosphino)ethane; silver(l) oxide; lithium hexamethyldisilazane; methyl iodide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; ammonia; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; xylene; tert-butyl alcohol; pentane; benzene; 1.1: Tosylation / 2.1: Metallation / 2.2: Condensation / 3.1: Substitution / 4.1: Reduction / 5.1: Substitution / 6.1: Epoxidation / 6.2: Cyclization / 7.1: Reduction / 7.2: Alkylation / 8.1: Substitution / 9.1: Oxidation / 10.1: Metallation / 10.2: Substitution / 10.3: Alkylation / 11.1: Hydrolysis / 12.1: Decarboxylation / 13.1: Isomerization / 14.1: Reduction / 15.1: Reduction / 16.1: Etherification / 17.1: Rearrangement / 18.1: Oxidation / 19.1: Cyclization / 20.1: Reduction / 21.1: Ring cle;

DOI:10.1135/cccc20000490

Reference yield:

oct-6-yn-1-ol (82402-15-1) → tert-Butyl (5R,6S,7R,7aR)-6-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-7-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]-2-oxo-4,5,6,7-tetrahydro-2H-1-benzofuran-3-propanoate (283611-59-6)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 97 percent / Li; NH₃

2.1: 58 percent / Ph₃P; I₂; imidazole / CH₂Cl₂

3.1: tert-BuLi / diethyl ether; pentane / 2 h / -78 - -10 °C

3.2: CuCN / pentane; diethyl ether; tetrahydrofuran / 2 h / -78 - -50 °C

3.3: 91 percent / BF₃*Et₂O / tetrahydrofuran; pentane; diethyl ether / -78 - -40 °C

4.1: aq. t-BuOK / tetrahydrofuran / 4.5 h / 20 °C

5.1: 51 percent / 0.17 h / 105 °C

6.1: 46 percent / Na₂CO₃ / methanol / 13.5 h / 75 °C

7.1: 91 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.17 h / 0 °C

8.1: 89 percent / Li / liquid ammonia; tetrahydrofuran / 0.5 h

9.1: 95 percent / Hg(OCOCF₃)2; Et₃N / 20 °C

10.1: 95 percent / xylene / 5 h / 170 °C

11.1: 99 percent / 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 5 h / 20 °C

12.1: 79 percent / NIS / CH₂Cl₂ / 3 h / -70 - 20 °C

13.1: 89 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

14.1: 78 percent / CH₃I; Ag₂O / CH₂Cl₂ / 2 h

15.1: 94 percent / NaBH₄ / methanol / 0.17 h / 0 °C

16.1: 83 percent / NaH / dimethylformamide / 36 h

17.1: 53 percent / camphorsulfonic acid; Et₃N / CH₂Cl₂; dimethylsulfoxide

18.1: 81 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

19.1: 83 percent / LHMDS / tetrahydrofuran / 8 h

With pyridine; 1H-imidazole; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-iodo-succinimide; cerium(III) chloride; 2-methyl-but-2-ene; camphor-10-sulfonic acid; potassium tert-butylate; ammonia; iodine; tert.-butyl lithium; mercury(II) trifluoroacetate; lithium; sodium hydride; diisobutylaluminium hydride; sodium carbonate; triethylamine; triphenylphosphine; silver(l) oxide; lithium hexamethyldisilazane; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ammonia; water; dimethyl sulfoxide; N,N-dimethyl-formamide; xylene; tert-butyl alcohol; pentane; 1.1: Reduction / 2.1: Substitution / 3.1: Metallation / 3.2: Substitution / 3.3: Alkylation / 4.1: Hydrolysis / 5.1: Decarboxylation / 6.1: Isomerization / 7.1: Reduction / 8.1: Reduction / 9.1: Etherification / 10.1: Rearrangement / 11.1: Oxidation / 12.1: Cyclization / 13.1: Reduction / 14.1: Ring cleavage / 15.1: Reduction / 16.1: Substitution / 17.1: Ring cleavage / 18.1: Substitution / 19.1: Cyclization;

DOI:10.1135/cccc20000490

upstream raw materials:

2-(Diethoxy-phosphoryl)-pentanedioic acid 5-tert-butyl ester 1-[(1R,2R,3S,4R)-3-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-ylmethyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-4-((E)-oct-6-enyl)-6-oxo-cyclohexyl] ester

pent-3-yn-1-ol

oct-6-yn-1-ol

(E)-2-octenyl alcohol