(E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide

Base Information

• Chemical Name: (E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide
• CAS No.: 724423-01-2
• Molecular Formula: C₃₁H₄₃NO₅
• Molecular Weight: 509.686
• Mol file: 724423-01-2.mol

Synonyms:(E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide

Chemical Property of (E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide

There total 20 articles about (E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide 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:

(+-)-2-methyl-pent-4-enoic acid (1575-74-2) → (E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide (724423-01-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: LiAlH₄ / tetrahydrofuran / 16 h / 20 °C

2.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

3.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C

3.2: 74 percent / K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran; dioxane / 5 h / 85 °C

4.1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

5.1: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

6.1: LiAlH₄ / diethyl ether / 0 - 20 °C

7.1: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

8.1: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

9.1: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.1: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

11.1: pyridinium dichromate / CH₂Cl₂ / 2 h / 20 °C

12.1: 29 mg / NaH / tetrahydrofuran / 1.25 h / 0 - 20 °C

13.1: 98 percent / H₂ / Pd/C / ethanol / 0.08 h / 760 Torr

14.1: LiHMDS / ethanol / 1.5 h / 0 - 20 °C

15.1: 140 mg / LiAlH₄ / diethyl ether / 1.08 h / 0 - 20 °C

16.1: 98 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 18 h / 20 °C

17.1: TBAF / tetrahydrofuran / 16.5 h / 0 - 20 °C

18.1: H₂SO₄; CrO₃ / acetone / 0.5 h / 0 °C

19.1: 44 mg / DMAP; EDCI; i-Pr₂NEt / CH₂Cl₂ / 16.5 h / 0 - 20 °C

With 1H-imidazole; chromium(VI) oxide; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; silver(l) oxide; lithium hexamethyldisilazane; dimeric 9-borabicyclo[3.3.1]nonane; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 3.2: Suzuki-Miyaura coupling / 4.1: Sharpless dihydroxylation / 12.1: Horner-Wadsworth-Emmons cyclization / 14.1: Wittig olefination / 18.1: Jones oxidation;

DOI:10.1021/jo048115z

Reference yield:

2-methylpent-4-en-1-ol (5673-98-3) → (E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide (724423-01-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C

2.2: 74 percent / K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran; dioxane / 5 h / 85 °C

3.1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

4.1: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

5.1: LiAlH₄ / diethyl ether / 0 - 20 °C

6.1: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

7.1: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

8.1: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

9.1: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

10.1: pyridinium dichromate / CH₂Cl₂ / 2 h / 20 °C

11.1: 29 mg / NaH / tetrahydrofuran / 1.25 h / 0 - 20 °C

12.1: 98 percent / H₂ / Pd/C / ethanol / 0.08 h / 760 Torr

13.1: LiHMDS / ethanol / 1.5 h / 0 - 20 °C

14.1: 140 mg / LiAlH₄ / diethyl ether / 1.08 h / 0 - 20 °C

15.1: 98 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 18 h / 20 °C

16.1: TBAF / tetrahydrofuran / 16.5 h / 0 - 20 °C

17.1: H₂SO₄; CrO₃ / acetone / 0.5 h / 0 °C

18.1: 44 mg / DMAP; EDCI; i-Pr₂NEt / CH₂Cl₂ / 16.5 h / 0 - 20 °C

With 1H-imidazole; chromium(VI) oxide; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; silver(l) oxide; lithium hexamethyldisilazane; dimeric 9-borabicyclo[3.3.1]nonane; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 2.2: Suzuki-Miyaura coupling / 3.1: Sharpless dihydroxylation / 11.1: Horner-Wadsworth-Emmons cyclization / 13.1: Wittig olefination / 17.1: Jones oxidation;

DOI:10.1021/jo048115z

Reference yield:

(Z)-ethyl 8-(tert-butyldiphenylsilanyloxy)-3,7-dimethyloct-2-enoate (724422-92-8) → (E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide (724423-01-2)

Guidance literature:

Multi-step reaction with 16 steps

1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

2: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

3: LiAlH₄ / diethyl ether / 0 - 20 °C

4: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

5: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

6: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

8: pyridinium dichromate / CH₂Cl₂ / 2 h / 20 °C

9: 29 mg / NaH / tetrahydrofuran / 1.25 h / 0 - 20 °C

10: 98 percent / H₂ / Pd/C / ethanol / 0.08 h / 760 Torr

11: LiHMDS / ethanol / 1.5 h / 0 - 20 °C

12: 140 mg / LiAlH₄ / diethyl ether / 1.08 h / 0 - 20 °C

13: 98 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 18 h / 20 °C

14: TBAF / tetrahydrofuran / 16.5 h / 0 - 20 °C

15: H₂SO₄; CrO₃ / acetone / 0.5 h / 0 °C

16: 44 mg / DMAP; EDCI; i-Pr₂NEt / CH₂Cl₂ / 16.5 h / 0 - 20 °C

With chromium(VI) oxide; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; silver(l) oxide; lithium hexamethyldisilazane; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 1: Sharpless dihydroxylation / 9: Horner-Wadsworth-Emmons cyclization / 11: Wittig olefination / 15: Jones oxidation;

DOI:10.1021/jo048115z

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

5-{(2S,3R)-3-Benzyloxy-6-[2-benzyloxy-eth-(E)-ylidene]-2-methyl-oxepan-2-yl}-2-methyl-pentanoic acid

(+-)-2-methyl-pent-4-enoic acid

2-methylpent-4-en-1-ol