Methanesulfonic acid (1S,4R,5R)-4-methanesulfonyloxy-5-methoxymethoxy-1-[(S)-1-methoxymethoxy-13-((S)-5-methyl-2-oxo-3-phenylsulfanyl-tetrahydro-furan-3-yl)-tridecyl]-heptadecyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,4R,5R)-4-methanesulfonyloxy-5-methoxymethoxy-1-[(S)-1-methoxymethoxy-13-((S)-5-methyl-2-oxo-3-phenylsulfanyl-tetrahydro-furan-3-yl)-tridecyl]-heptadecyl ester
• CAS No.: 1054618-92-6
• Molecular Formula: C₄₇H₈₄O₁₂S₃
• Molecular Weight: 937.375
• Mol file: 1054618-92-6.mol

Synonyms:

Chemical Property of Methanesulfonic acid (1S,4R,5R)-4-methanesulfonyloxy-5-methoxymethoxy-1-[(S)-1-methoxymethoxy-13-((S)-5-methyl-2-oxo-3-phenylsulfanyl-tetrahydro-furan-3-yl)-tridecyl]-heptadecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1S,4R,5R)-4-methanesulfonyloxy-5-methoxymethoxy-1-[(S)-1-methoxymethoxy-13-((S)-5-methyl-2-oxo-3-phenylsulfanyl-tetrahydro-furan-3-yl)-tridecyl]-heptadecyl ester

There total 21 articles about Methanesulfonic acid (1S,4R,5R)-4-methanesulfonyloxy-5-methoxymethoxy-1-[(S)-1-methoxymethoxy-13-((S)-5-methyl-2-oxo-3-phenylsulfanyl-tetrahydro-furan-3-yl)-tridecyl]-heptadecyl 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:

2-nonyn-1-ol (5921-73-3) → Methanesulfonic acid (1S,4R,5R)-4-methanesulfonyloxy-5-methoxymethoxy-1-[(S)-1-methoxymethoxy-13-((S)-5-methyl-2-oxo-3-phenylsulfanyl-tetrahydro-furan-3-yl)-tridecyl]-heptadecyl ester (1054618-92-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / KNH(CH₂)3NH₂

2: imidazole / dimethylformamide

3: 1.) n-Bu₃SnH, AIBN; 2.) I₂

4: TBAF / tetrahydrofuran

5: pyridine

6: NaI / acetone

7: 60 percent / NaHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide

8: 53 percent / CuI, pyrrolidine / Pd(Ph₃P)4

9: 77 percent / H₂ / Rh(Ph₃P)3Cl / benzene

10: Et₃N / CH₂Cl₂

With pyrrolidine; pyridine; 1H-imidazole; copper(l) iodide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; iodine; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; potassium salt of 1,3-diaminopropane; triethylamine; sodium iodide; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/0040-4039(96)01086-6

Reference yield:

8-nonyn-1-ol (10160-28-8) → Methanesulfonic acid (1S,4R,5R)-4-methanesulfonyloxy-5-methoxymethoxy-1-[(S)-1-methoxymethoxy-13-((S)-5-methyl-2-oxo-3-phenylsulfanyl-tetrahydro-furan-3-yl)-tridecyl]-heptadecyl ester (1054618-92-6)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole / dimethylformamide

2: 1.) n-Bu₃SnH, AIBN; 2.) I₂

3: TBAF / tetrahydrofuran

4: pyridine

5: NaI / acetone

6: 60 percent / NaHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide

7: 53 percent / CuI, pyrrolidine / Pd(Ph₃P)4

8: 77 percent / H₂ / Rh(Ph₃P)3Cl / benzene

9: Et₃N / CH₂Cl₂

With pyrrolidine; pyridine; 1H-imidazole; copper(l) iodide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; iodine; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; triethylamine; sodium iodide; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/0040-4039(96)01086-6

Reference yield:

(-)-(4R,5R)-muricatacin (134698-86-5) → Methanesulfonic acid (1S,4R,5R)-4-methanesulfonyloxy-5-methoxymethoxy-1-[(S)-1-methoxymethoxy-13-((S)-5-methyl-2-oxo-3-phenylsulfanyl-tetrahydro-furan-3-yl)-tridecyl]-heptadecyl ester (1054618-92-6)

Guidance literature:

Multi-step reaction with 17 steps

1: i-Pr₂NEt / CH₂Cl₂

2: DIBAL / CH₂Cl₂

3: 76 percent / NaH / tetrahydrofuran / -78 °C

4: PPTS / CH₂Cl₂

5: AD-mix α, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O

6: PPTS / CH₂Cl₂

7: LiAlH₄ / diethyl ether

8: pyridine

9: PPTS / methanol

10: KOH

11: 98 percent / PPTS / CH₂Cl₂

12: 96 percent / BF₃*Et₂O / tetrahydrofuran

13: i-Pr₂NEt / CH₂Cl₂

14: PPTS / methanol

15: 53 percent / CuI, pyrrolidine / Pd(Ph₃P)4

16: 77 percent / H₂ / Rh(Ph₃P)3Cl / benzene

17: Et₃N / CH₂Cl₂

With pyrrolidine; pyridine; potassium hydroxide; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; methanesulfonamide; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1016/0040-4039(96)01086-6

upstream raw materials:

2-nonyn-1-ol

8-nonyn-1-ol

(-)-(4R,5R)-muricatacin

(5R,5'R)-(2',4'-dioxaheptadecan-5'-yl)tetrahydrofuran-2-one