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

Base Information

• Chemical Name: 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
• CAS No.: 283611-65-4
• Molecular Formula: C₄₈H₇₇O₁₂P
• Molecular Weight: 877.106

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 29 articles about 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 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: 81.0%

4-chlorocarbonyl-4-(diethoxy-phosphoryl)-butyric acid tert-butyl ester (283611-58-5) + (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) → 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)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1135/cccc20000490

Reference yield:

pent-3-yn-1-ol (10229-10-4) → 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)

Guidance literature:

Multi-step reaction with 25 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

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) → 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)

Guidance literature:

Multi-step reaction with 18 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

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; 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;

DOI:10.1135/cccc20000490

upstream raw materials:

4-chlorocarbonyl-4-(diethoxy-phosphoryl)-butyric acid tert-butyl ester

(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

pent-3-yn-1-ol

oct-6-yn-1-ol

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

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