(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

Base Information

• Chemical Name: (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
• CAS No.: 283611-57-4
• Molecular Formula: C₃₅H₅₄O₆
• Molecular Weight: 570.81

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 27 articles about (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 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: 53.0%

(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) → (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 (283611-57-4)

Guidance literature:

With camphor-10-sulfonic acid; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1135/cccc20000490

Reference yield:

pent-3-yn-1-ol (10229-10-4) → (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 (283611-57-4)

Guidance literature:

Multi-step reaction with 24 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

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; 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) → (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 (283611-57-4)

Guidance literature:

Multi-step reaction with 17 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

With 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; 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;

DOI:10.1135/cccc20000490

upstream raw materials:

(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

pent-3-yn-1-ol

oct-6-yn-1-ol

(E)-2-octenyl alcohol

Downstream raw materials:

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

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 283611-57-4 (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

Send

Send

Metric Ton KG G Pound L ML

Send

Send