(4S,5S)-4-{[(1S,2R,3R,4S,6R)-3,4-Epoxy-2-{2-[(4-methoxybenzyl)oxy]ethyl}-6-[(E)-oct-6-en-1-yl]cyclohexyl]methyl}-2,2-dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolane

Base Information

• Chemical Name: (4S,5S)-4-{[(1S,2R,3R,4S,6R)-3,4-Epoxy-2-{2-[(4-methoxybenzyl)oxy]ethyl}-6-[(E)-oct-6-en-1-yl]cyclohexyl]methyl}-2,2-dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolane
• CAS No.: 283611-56-3
• Molecular Formula: C₃₅H₅₄O₅
• Molecular Weight: 554.811
• Mol file: 283611-56-3.mol

Synonyms:

Chemical Property of (4S,5S)-4-{[(1S,2R,3R,4S,6R)-3,4-Epoxy-2-{2-[(4-methoxybenzyl)oxy]ethyl}-6-[(E)-oct-6-en-1-yl]cyclohexyl]methyl}-2,2-dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-{[(1S,2R,3R,4S,6R)-3,4-Epoxy-2-{2-[(4-methoxybenzyl)oxy]ethyl}-6-[(E)-oct-6-en-1-yl]cyclohexyl]methyl}-2,2-dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolane

There total 26 articles about (4S,5S)-4-{[(1S,2R,3R,4S,6R)-3,4-Epoxy-2-{2-[(4-methoxybenzyl)oxy]ethyl}-6-[(E)-oct-6-en-1-yl]cyclohexyl]methyl}-2,2-dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolane 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%

p-methoxybenzyl chloride (824-94-2) + (1R,2S,3R,5S,6R)-2-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-5,6-epoxy-3-[(E)-oct-6-en-1-yl]-1-ethanol (283611-55-2) → (4S,5S)-4-{[(1S,2R,3R,4S,6R)-3,4-Epoxy-2-{2-[(4-methoxybenzyl)oxy]ethyl}-6-[(E)-oct-6-en-1-yl]cyclohexyl]methyl}-2,2-dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolane (283611-56-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 36h;

DOI:10.1135/cccc20000490

Reference yield:

pent-3-yn-1-ol (10229-10-4) → (4S,5S)-4-{[(1S,2R,3R,4S,6R)-3,4-Epoxy-2-{2-[(4-methoxybenzyl)oxy]ethyl}-6-[(E)-oct-6-en-1-yl]cyclohexyl]methyl}-2,2-dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolane (283611-56-3)

Guidance literature:

Multi-step reaction with 23 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

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; 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; methyl iodide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; ammonia; water; 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) → (4S,5S)-4-{[(1S,2R,3R,4S,6R)-3,4-Epoxy-2-{2-[(4-methoxybenzyl)oxy]ethyl}-6-[(E)-oct-6-en-1-yl]cyclohexyl]methyl}-2,2-dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolane (283611-56-3)

Guidance literature:

Multi-step reaction with 16 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

With 1H-imidazole; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-iodo-succinimide; cerium(III) chloride; 2-methyl-but-2-ene; potassium tert-butylate; ammonia; iodine; tert.-butyl lithium; mercury(II) trifluoroacetate; lithium; sodium hydride; diisobutylaluminium hydride; sodium carbonate; triethylamine; triphenylphosphine; silver(l) oxide; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ammonia; water; 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;

DOI:10.1135/cccc20000490

upstream raw materials:

p-methoxybenzyl chloride

(1R,2S,3R,5S,6R)-2-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-5,6-epoxy-3-[(E)-oct-6-en-1-yl]-1-ethanol

pent-3-yn-1-ol

oct-6-yn-1-ol

Downstream raw materials:

(2R,3R,4S,5R)-4-{[(4S,5S)-2,2-Dimethyl-5-[(E)-pent-3-en-1-yl]-1,3-dioxolan-4-yl]methyl}-2-hydroxy-3-{2-[(4-methoxybenzyl)oxy]ethyl}-5-[(E)-oct-6-en-1-yl]cyclohexan-1-one

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

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