(4S,5R,6R)-5-AcetaMido-4-aMino-6-((1R,2R)-2,3-dihydroxy-1-Methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic Acid

Base Information

• Chemical Name: (4S,5R,6R)-5-AcetaMido-4-aMino-6-((1R,2R)-2,3-dihydroxy-1-Methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic Acid
• CAS No.: 475483-21-7
• Molecular Formula: C₁₂H₂₀N₂O₇
• Molecular Weight: 304.3
• Mol file: 475483-21-7.mol

Synonyms:(4S,5R,6R)-5-AcetaMido-4-aMino-6-((1R,2R)-2,3-dihydroxy-1-Methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic Acid

Chemical Property of (4S,5R,6R)-5-AcetaMido-4-aMino-6-((1R,2R)-2,3-dihydroxy-1-Methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic Acid

Chemical Property:

• PSA: 151.34000
• LogP: -1.35490
• Storage Temp.: -20°C Freezer
• Solubility.: Water

Purity/Quality:

95% ^*data from raw suppliers

(4S,5R,6R)-5-Acetamido-4-amino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (4S,5R,6R)-5-Acetamido-4-amino-6-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic Acid is an intermediate in the preparation of Neuraminic Acid and its derivatives.

Technology Process of (4S,5R,6R)-5-AcetaMido-4-aMino-6-((1R,2R)-2,3-dihydroxy-1-Methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic Acid

There total 4 articles about (4S,5R,6R)-5-AcetaMido-4-aMino-6-((1R,2R)-2,3-dihydroxy-1-Methoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic Acid 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:

methyl (4S,5R,6R)-5-acetylamino-4-amino-6-[(S)-methoxy-((R)-2-oxo-[1,3]dioxolan-4-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylate (1072449-88-7) → (2R,3R,4S)-3-acetamide-4-amino-2-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid (475483-21-7)

Guidance literature:

methyl (4S,5R,6R)-5-acetylamino-4-amino-6-[(S)-methoxy-((R)-2-oxo-[1,3]dioxolan-4-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylate; With sodium hydroxide; water; In tetrahydrofuran; at 50 ℃; for 2h;

With hydrogenchloride; water; In tetrahydrofuran; at 0 ℃;

Reference yield:

methyl (2R,3R,4S)-3-acetamide-4-azide-2-{(S)-methoxy[(4R)-2-oxo-1,3-dioxolan-4-yl]methyl}-3,4-dihydro-2H-pyran-6-carboxylate → (2R,3R,4S)-3-acetamide-4-amino-2-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid (475483-21-7)

Guidance literature:

methyl (2R,3R,4S)-3-acetamide-4-azide-2-{(S)-methoxy[(4R)-2-oxo-1,3-dioxolan-4-yl]methyl}-3,4-dihydro-2H-pyran-6-carboxylate; With triphenylphosphine; In tetrahydrofuran; at 20 - 40 ℃; for 2h;

With water; sodium hydroxide; In tetrahydrofuran; at 40 ℃; for 2h;

With hydrogenchloride; water; In tetrahydrofuran; ethyl acetate; at 25 ℃;

Reference yield:

methyl (3aS,4R,7aR)-4-{(S)-hydroxy-((4R)-2-oxo-1,3-dioxolan-4-yl)methyl}-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate (1072449-84-3) → (2R,3R,4S)-3-acetamide-4-amino-2-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid (475483-21-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl acetamide; mineral oil / 3 h / 3 °C

2.1: titanium(IV) isopropylate; trimethylsilylazide / toluene; tert-butyl alcohol / 15 h / 18 °C

2.2: 1 h / 20 °C

3.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 - 40 °C

3.2: 2 h / 40 °C

3.3: 25 °C

With titanium(IV) isopropylate; trimethylsilylazide; sodium hydride; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl acetamide; toluene; mineral oil; tert-butyl alcohol;

upstream raw materials:

methyl (4S,5R,6R)-5-acetylamino-4-amino-6-[(S)-methoxy-((R)-2-oxo-[1,3]dioxolan-4-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylate

methyl (3aS,4R,7aR)-4-{(S)-hydroxy-((4R)-2-oxo-1,3-dioxolan-4-yl)methyl}-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate

methyl (3aR,4R,7aR)-4-{(S)-methoxy[(4R)-2-oxo-1,3-dioxolan-4-yl]methyl}-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate

Downstream raw materials:

Laninamivir

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