(5S)-3-[7-[(5S)-5-[(4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]tetrahydrofuran-2-yl]butyl]tetrahydrofuran-2-yl]heptyl]-5-methyl-5H-furan-2-one

Base Information

• Chemical Name: (5S)-3-[7-[(5S)-5-[(4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]tetrahydrofuran-2-yl]butyl]tetrahydrofuran-2-yl]heptyl]-5-methyl-5H-furan-2-one
• CAS No.: 143572-82-1
• Molecular Formula: C₃₇H₆₆O₇
• Molecular Weight: 622.927

Synonyms:2(5H)-Furanone,3-[7-[5-[1,4-dihydroxy-4-[tetrahydro-5-(1-hydroxytridecyl)-2-furanyl]butyl]tetrahydro-2-furanyl]heptyl]-5-methyl-,[2R-[2a(S*),5b[1S*,4R*[2R*,5R*(R*)]]]]-; (+)-4-Deoxygigantecin;4-Deoxygigantecin

Chemical Property of (5S)-3-[7-[(5S)-5-[(4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]tetrahydrofuran-2-yl]butyl]tetrahydrofuran-2-yl]heptyl]-5-methyl-5H-furan-2-one

Chemical Property:

• Vapor Pressure: 6.15E-26mmHg at 25°C
• Boiling Point: 749.6°Cat760mmHg
• Flash Point: 221.9°C
• Density: 1.045g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (5S)-3-[7-[(5S)-5-[(4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]tetrahydrofuran-2-yl]butyl]tetrahydrofuran-2-yl]heptyl]-5-methyl-5H-furan-2-one

There total 24 articles about (5S)-3-[7-[(5S)-5-[(4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxytridecyl]tetrahydrofuran-2-yl]butyl]tetrahydrofuran-2-yl]heptyl]-5-methyl-5H-furan-2-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:

(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one (184435-75-4) → (+)-4-deoxygigantecin (143572-82-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

1.2: 89 percent / tetrahydrofuran; toluene; hexamethylphosphoric acid triamide / 6 h / 0 - 20 °C

2.1: 96 percent / p-TsOH*H₂O / methanol / 8 h / 20 °C

3.1: mCPBA / 1,2-dichloro-ethane / 0.25 h / 0 °C

4.1: 720 mg / toluene / 0.5 h / Heating

5.1: 95 percent / Dess-Martin periodinane / 1,2-dichloro-ethane / 0.25 h / 20 °C

6.1: 85 percent / CrCl₂ / tetrahydrofuran / 8 h / 20 °C

7.1: 66 percent / Et₃N; CuI / Pd(PPh₃)4 / benzene; tetrahydrofuran / 2 h / 20 °C

8.1: H₂ / Rh(PPh₃)3Cl / benzene / 8 h

9.1: 1.0 mg / Me₂S; BF₃*Et₂O / 0.08 h / 0 °C

With chromium dichloride; copper(l) iodide; dimethylsulfide; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; toluene; benzene; 1.1: Metallation / 1.2: Alkylation / 2.1: deprotection / 3.1: Oxidation / 4.1: Elimination / 5.1: Dess-Martin oxidation / 6.1: Condensation / 7.1: Condensation / 8.1: Catalytic hydrogenation / 9.1: deprotection;

DOI:10.1016/S0040-4020(98)00285-3

Reference yield:

2-(1'-benzoyloxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran (158664-34-7) → (+)-4-deoxygigantecin (143572-82-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 91 percent / NaOH / methanol / 8 h / 20 °C

2.1: 94 percent / i-Pr₂NEt / CH₂Cl₂ / 12 h

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -10 - 0 °C

3.2: 70 percent / tetrahydrofuran; hexane / 3 h / 0 - 20 °C

4.1: 94 percent / Na / liquid ammonia; tetrahydrofuran; 2-methyl-propan-2-ol / 8 h / -40 °C

5.1: 96 percent / aq. AcOH / 1 h / 60 °C

6.1: 95 percent / DMAP; Et₃N / CH₂Cl₂ / 12 h

7.1: Et₃N / CH₂Cl₂ / 0.17 h / -10 °C

8.1: 77 mg / TBAF / tetrahydrofuran / 10 h / 0 - 20 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: BF₃*Et₂O / tetrahydrofuran; hexane / 1 h

10.1: 69 mg / TBAF / tetrahydrofuran / 5 h / 0 - 20 °C

11.1: Et₃N / CH₂Cl₂ / 0.17 h / -10 °C

12.1: AD mix α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 0 °C

13.1: 18 mg / Triton B / methanol / 24 h

14.1: 66 percent / Et₃N; CuI / Pd(PPh₃)4 / benzene; tetrahydrofuran / 2 h / 20 °C

15.1: H₂ / Rh(PPh₃)3Cl / benzene / 8 h

16.1: 1.0 mg / Me₂S; BF₃*Et₂O / 0.08 h / 0 °C

With dmap; sodium hydroxide; AD-mix-α; copper(l) iodide; n-butyllithium; dimethylsulfide; methanesulfonamide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium; N-benzyl-trimethylammonium hydroxide; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; ammonia; water; tert-butyl alcohol; benzene; 1.1: Hydrolysis / 2.1: Etherification / 3.1: Metallation / 3.2: Alkylation / 4.1: Reduction / 5.1: Hydrolysis / 6.1: silylation / 7.1: mesylation / 8.1: Epoxidation / 9.1: Metallation / 9.2: Ring cleavage / 10.1: desilylation / 11.1: mesylation / 12.1: Sharpless dihydroxylation / 13.1: Cyclization / 14.1: Condensation / 15.1: Catalytic hydrogenation / 16.1: deprotection;

DOI:10.1016/S0040-4020(98)00285-3

Reference yield:

(S)-3-(3'-hydroxypropyl)-5-methyl-2,5-dihydrofuran-2-one (191993-25-6) → (+)-4-deoxygigantecin (143572-82-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / Dess-Martin periodinane / 1,2-dichloro-ethane / 0.25 h / 20 °C

2: 85 percent / CrCl₂ / tetrahydrofuran / 8 h / 20 °C

3: 66 percent / Et₃N; CuI / Pd(PPh₃)4 / benzene; tetrahydrofuran / 2 h / 20 °C

4: H₂ / Rh(PPh₃)3Cl / benzene / 8 h

5: 1.0 mg / Me₂S; BF₃*Et₂O / 0.08 h / 0 °C

With chromium dichloride; copper(l) iodide; dimethylsulfide; boron trifluoride diethyl etherate; hydrogen; Dess-Martin periodane; triethylamine; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dichloro-ethane; benzene; 1: Dess-Martin oxidation / 2: Condensation / 3: Condensation / 4: Catalytic hydrogenation / 5: deprotection;

DOI:10.1016/S0040-4020(98)00285-3

upstream raw materials:

(S)-3-[7-((2R,5S)-5-{(1S,4R)-1-Hydroxy-4-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-heptyl]-5-methyl-5H-furan-2-one

(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one

2-(1'-benzoyloxy-4'-pentynyl)-5-(1''-methoxymethoxytridecyl)tetrahydrofuran

(S)-3-(3'-hydroxypropyl)-5-methyl-2,5-dihydrofuran-2-one

Refernces

Total synthesis of (+)-4-deoxygigantecin

10.1016/S0040-4039(97)00856-3

The study reports the first total synthesis of the natural product (+)-4-deoxygigantecin (1), a non-adjacent bis-tetrahydrofuran type annonaceous acetogenin. The synthesis began with enantiomerically pure (-)-muricatacin (3), which was converted through a series of reactions into key intermediate 5. This intermediate was then transformed into the final product via the formation of a bis-tetrahydrofuran unit 11 and a coupling reaction with iodo lactone synthon 16. The study highlights the use of various reagents and conditions, such as MOM ether for protection, n-BuLi for alkylation, Na in liquid ammonia for reduction, and the Sharpless asymmetric dihydroxylation for selective hydroxylation. The final product was obtained in 95% overall yield and its properties were consistent with those of the natural compound, demonstrating the successful synthesis of a complex natural product with significant biological activities.

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