Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester
• CAS No.: 325740-69-0
• Molecular Formula: C₂₆H₄₂O₈S
• Molecular Weight: 514.681

Synonyms:Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester

Chemical Property of Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester

There total 15 articles about Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl 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:

(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid (172900-71-9) → Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester (325740-69-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / NaBH₄; I₂ / 96 h / 20 °C

2: 70 percent / SOCl₂; pyridine

3: Mg; BrCH₂CH₂Br / tetrahydrofuran / 20 °C

4: H₂ / [Ru₂Cl₄((S)-BINAP)]NEt₃ / methanol / 40 h / 40 °C / 37503 Torr

5: NEt₃ / CH₂Cl₂

With pyridine; sodium tetrahydroborate; thionyl chloride; hydrogen; iodine; magnesium; ethylene dibromide; triethylamine; [Ru₂Cl₄((S)-BINAP)]NEt₃; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)01794-9

Reference yield:

(S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (145589-03-3,104266-90-2) → Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester (325740-69-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 94 percent / LIHMDS / tetrahydrofuran / -78 °C

2: 88 percent / OsO₄; NMMO / 2-methyl-propan-2-ol; acetone; H₂O

3: NaIO₄; RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 6 h

4: (COCl)2 / dimethylformamide; toluene / 1 h

5: NEt₃ / CH₂Cl₂

6: 100 percent / H₂ / Pd/C / ethyl acetate

7: (COCl)2 / toluene; dimethylformamide / 1 h

8: Mg; BrCH₂CH₂Br / tetrahydrofuran / 20 °C

9: H₂ / [Ru₂Cl₄((S)-BINAP)]NEt₃ / methanol / 40 h / 40 °C / 37503 Torr

10: NEt₃ / CH₂Cl₂

With ruthenium trichloride; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; hydrogen; magnesium; 4-methylmorpholine N-oxide; ethylene dibromide; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; [Ru₂Cl₄((S)-BINAP)]NEt₃; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)01794-9

Reference yield:

(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-isopropyl-dihydro-furan-2-one (191152-26-8) → Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester (325740-69-0)

Guidance literature:

Multi-step reaction with 6 steps

1: TBAF / tetrahydrofuran / 73 °C

2: 96 percent / NaIO₄; RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 6 h

3: (COCl)2 / toluene; dimethylformamide / 1 h

4: Mg; BrCH₂CH₂Br / tetrahydrofuran / 20 °C

5: H₂ / [Ru₂Cl₄((S)-BINAP)]NEt₃ / methanol / 40 h / 40 °C / 37503 Torr

6: NEt₃ / CH₂Cl₂

With ruthenium trichloride; sodium periodate; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; magnesium; ethylene dibromide; triethylamine; [Ru₂Cl₄((S)-BINAP)]NEt₃; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)01794-9

upstream raw materials:

methanesulfonyl chloride

(3S,5S)-dihydro-5-{(1S,3S)-1-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-3-(1-methylethyl)furan-2(3H)-one

(S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one

(3S,5S)-5-Hydroxymethyl-3-isopropyl-dihydro-furan-2-one

Downstream raw materials:

(3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one

(2S,4S,5R,7S)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methyl-2-isopropylnonanamide

(2S,4S,5R,7S)-5-Azido-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

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