(2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((1S,2S)-1-benzylcarbamoyl-2-methyl-butyl)-amide

Base Information

• Chemical Name: (2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((1S,2S)-1-benzylcarbamoyl-2-methyl-butyl)-amide
• CAS No.: 1056676-15-3
• Molecular Formula: C₂₉H₄₁N₅O₄
• Molecular Weight: 523.676
• Mol file: 1056676-15-3.mol

Synonyms:(2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((1S,2S)-1-benzylcarbamoyl-2-methyl-butyl)-amide

Chemical Property of (2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((1S,2S)-1-benzylcarbamoyl-2-methyl-butyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((1S,2S)-1-benzylcarbamoyl-2-methyl-butyl)-amide

There total 11 articles about (2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((1S,2S)-1-benzylcarbamoyl-2-methyl-butyl)-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: 70.0%

(3S,5S)-5-[(1S)-1-azido-2-benzyloxyethyl]-3-isopropyldihydrofuran-2-one (1000045-28-2) + (2S,3S)-2-amino-N-benzyl-3-methylpentanamide (129253-02-7) → (2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((1S,2S)-1-benzylcarbamoyl-2-methyl-butyl)-amide (1056676-15-3)

Guidance literature:

With 2-hydroxypyridin; N-ethyl-N,N-diisopropylamine; at 70 ℃; for 72h;

Reference yield:

5,6-di-O-benzyl-2,3-dideoxy-D-glucono-1,4-lactone (1056674-35-1) → (2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((1S,2S)-1-benzylcarbamoyl-2-methyl-butyl)-amide (1056676-15-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; tris(pyrrolidino)phosphine oxide / -60 °C

2.1: hydrogen / palladium 10% on activated carbon / methanol / 2250.23 Torr

3.1: di(n-butyl)tin oxide / toluene / 4 h / Heating / reflux

3.2: 22 h / 90 °C

4.1: pyridine / dichloromethane / 0.25 - 0.5 h / 0 - 20 °C

5.1: sodium azide / N,N-dimethyl-formamide / 1 h / 60 °C

6.1: 2-hydroxypyridin; N-ethyl-N,N-diisopropylamine / 72 h / 70 °C

With pyridine; 2-hydroxypyridin; sodium azide; hydrogen; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; tris(pyrrolidino)phosphine oxide; N,N-dimethyl-formamide; toluene;

Reference yield:

methyl 5,6-di-O-benzyl-3-deoxy-α-D-glucofuranoside (1056674-18-0) → (2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((1S,2S)-1-benzylcarbamoyl-2-methyl-butyl)-amide (1056676-15-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tetrahydrofuran / 2 h / Heating / reflux

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.33 h / 100 °C

3.1: boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 17 h / 0 - 20 °C

4.1: lithium diisopropyl amide / tetrahydrofuran; tris(pyrrolidino)phosphine oxide / -60 °C

5.1: hydrogen / palladium 10% on activated carbon / methanol / 2250.23 Torr

6.1: di(n-butyl)tin oxide / toluene / 4 h / Heating / reflux

6.2: 22 h / 90 °C

7.1: pyridine / dichloromethane / 0.25 - 0.5 h / 0 - 20 °C

8.1: sodium azide / N,N-dimethyl-formamide / 1 h / 60 °C

9.1: 2-hydroxypyridin; N-ethyl-N,N-diisopropylamine / 72 h / 70 °C

With pyridine; 2-hydroxypyridin; sodium azide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; tris(pyrrolidino)phosphine oxide; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(3S,5S)-5-[(1S)-1-azido-2-benzyloxyethyl]-3-isopropyldihydrofuran-2-one

(2S,3S)-2-amino-N-benzyl-3-methylpentanamide

(3S,5S)-5-((R)-1,2-dihydroxyethyl)-3-isopropyldihydrofuran-2(3H)-one

(3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-one

Refernces