(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

Base Information

• Chemical Name: (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
• CAS No.: 325154-31-2
• Molecular Formula: C₃₀H₅₁N₅O₆
• Molecular Weight: 577.765
• Mol file: 325154-31-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 16 articles about (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 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) → (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 (325154-31-2)

Guidance literature:

Multi-step reaction with 7 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

6: 85 percent / NaN₃; 15-crown-6; DMPU

7: 59 percent / 2-OH-pyridine; NEt₃

With pyridine; 2-hydroxypyridin; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; thionyl chloride; sodium azide; 15-crown-6; 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) → (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 (325154-31-2)

Guidance literature:

Multi-step reaction with 12 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

11: 85 percent / NaN₃; 15-crown-6; DMPU

12: 59 percent / 2-OH-pyridine; NEt₃

With 2-hydroxypyridin; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; sodium azide; oxalyl dichloride; 15-crown-6; 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-Hydroxymethyl-3-isopropyl-dihydro-furan-2-one (191152-27-9,191152-30-4,325740-73-6) → (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 (325154-31-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / NaIO₄; RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 6 h

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

3: Mg; BrCH₂CH₂Br / tetrahydrofuran / 20 °C

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

5: NEt₃ / CH₂Cl₂

6: 85 percent / NaN₃; 15-crown-6; DMPU

7: 59 percent / 2-OH-pyridine; NEt₃

With 2-hydroxypyridin; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ruthenium trichloride; sodium periodate; sodium azide; oxalyl dichloride; 15-crown-6; 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:

aliskiren

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