(1R,3S)-1-[(2S,4S)-4-Isopropyl-5-oxotetrahydro-2-furanyl]-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl methanesulfonate

Base Information

• Chemical Name: (1R,3S)-1-[(2S,4S)-4-Isopropyl-5-oxotetrahydro-2-furanyl]-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl methanesulfonate
• CAS No.: 325740-68-9
• Molecular Formula: C₂₆H₄₂O₈S
• Molecular Weight: 514.681
• DSSTox Substance ID: DTXSID601335329
• Mol file: 325740-68-9.mol

Synonyms:DTXSID601335329;(1R,3S)-1-[(2S,4S)-4-Isopropyl-5-oxotetrahydro-2-furanyl]-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl methanesulfonate;325740-68-9

Chemical Property of (1R,3S)-1-[(2S,4S)-4-Isopropyl-5-oxotetrahydro-2-furanyl]-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl methanesulfonate

Chemical Property:

• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 15
• Exact Mass: 514.26003947
• Heavy Atom Count: 35
• Complexity: 732

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1CC(OC1=O)C(CC(CC2=CC(=C(C=C2)OC)OCCCOC)C(C)C)OS(=O)(=O)C
• Isomeric SMILES: CC(C)[C@@H]1C[C@H](OC1=O)[C@@H](C[C@H](CC2=CC(=C(C=C2)OC)OCCCOC)C(C)C)OS(=O)(=O)C

Technology Process of (1R,3S)-1-[(2S,4S)-4-Isopropyl-5-oxotetrahydro-2-furanyl]-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl methanesulfonate

There total 14 articles about (1R,3S)-1-[(2S,4S)-4-Isopropyl-5-oxotetrahydro-2-furanyl]-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl methanesulfonate 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 (1R,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester (325740-68-9)

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 (1R,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester (325740-68-9)

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 (1R,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester (325740-68-9)

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:

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

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

(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-isopropyl-dihydro-furan-2-one

(4S)-3-[(2S)-2-(1-methylethyl)-1-oxopent-4-en-1-yl]-4-(phenylmethyl)oxazolidin-2-one

Downstream raw materials:

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

(2S,4S,5S,7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-5-azido-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(methoxypropoxy)benzyl)-8-methylnonanamide

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

Refernces