5-(Acetylamino)-2,7-anhydro-3,5-dideoxy-D-glycero-alpha-D-galacto-2-Nonulopyranosonic acid

Base Information

• Chemical Name: 5-(Acetylamino)-2,7-anhydro-3,5-dideoxy-D-glycero-alpha-D-galacto-2-Nonulopyranosonic acid
• CAS No.: 95574-95-1
• Molecular Formula: C₁₁H₁₇NO₈
• Molecular Weight: 291.258
• Mol file: 95574-95-1.mol

Synonyms:2,7-AHANA;2,7-anhydro-N-acetylneuraminic acid;2,7-anhydro-Neu5Ac

Chemical Property of 5-(Acetylamino)-2,7-anhydro-3,5-dideoxy-D-glycero-alpha-D-galacto-2-Nonulopyranosonic acid

Chemical Property:

• Vapor Pressure: 6.95E-25mmHg at 25°C
• Boiling Point: 734.2°Cat760mmHg
• PKA: 1.99±0.70(Predicted)
• Flash Point: 397.8°C
• PSA: 145.55000
• Density: 1.61g/cm³
• LogP: -2.43530
• XLogP3: -3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 291.09541650
• Heavy Atom Count: 20
• Complexity: 415

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(CC2(OC1C(O2)C(CO)O)C(=O)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](CC2(O[C@@H](C1O2)[C@@H](CO)O)C(=O)O)O

Technology Process of 5-(Acetylamino)-2,7-anhydro-3,5-dideoxy-D-glycero-alpha-D-galacto-2-Nonulopyranosonic acid

There total 6 articles about 5-(Acetylamino)-2,7-anhydro-3,5-dideoxy-D-glycero-alpha-D-galacto-2-Nonulopyranosonic 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: 95.0%

(1R,2R,3S,5S)-2-Acetylamino-7-((R)-1,2-dihydroxy-ethyl)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid methyl ester (83236-80-0) → 2,7-anhydro-N-acetylneuraminic acid (95574-95-1)

Guidance literature:

With sodium hydroxide; at 35 ℃; for 3h;

DOI:10.1248/cpb.39.817

Reference yield:

methyl 5-acetamido, 3,5-dideoxy-8,9-O-isopropylidene-Dglycero-β-D-galacto-2-nonulopyranosonate (114857-70-4) → 2,7-anhydro-N-acetylneuraminic acid (95574-95-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / pyridine

2: 75 percent / 4-N,N-dimethylaminopyridine / acetonitrile

3: 45 percent / AgOTf / (MeCN)2Pd(II)Cl₂ / MS 4A / CH₂Cl₂

4: 80percent AcOH / H₂O / 2 h / 40 °C

5: 2percent MeONa-MeOH / 4 h / 25 °C

6: 95 percent / 0.5 N NaOH / 3 h / 35 °C

With pyridine; methanol; dmap; dichloro bis(acetonitrile) palladium(II); sodium hydroxide; sodium methylate; silver trifluoromethanesulfonate; acetic acid; In dichloromethane; water; acetonitrile;

DOI:10.1248/cpb.39.817

Reference yield:

methyl (5-acetamido-2,7-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-isopropylidene-α-D-glycero-D-galacto-2-nonulopyranosid)onate (134699-91-5) → 2,7-anhydro-N-acetylneuraminic acid (95574-95-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 80percent AcOH / H₂O / 2 h / 40 °C

2: 2percent MeONa-MeOH / 4 h / 25 °C

3: 95 percent / 0.5 N NaOH / 3 h / 35 °C

With methanol; sodium hydroxide; sodium methylate; acetic acid; In water;

DOI:10.1248/cpb.39.817

upstream raw materials:

(1R,2R,3S,5S)-2-Acetylamino-7-((R)-1,2-dihydroxy-ethyl)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid methyl ester

methyl 5-acetamido, 3,5-dideoxy-8,9-O-isopropylidene-Dglycero-β-D-galacto-2-nonulopyranosonate

methyl (5-acetamido-2,7-anhydro-4-O-benzoyl-3,5-dideoxy-8,9-isopropylidene-α-D-glycero-D-galacto-2-nonulopyranosid)onate

(2S,4S,5R,6R)-5-Acetylamino-4-benzoyloxy-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Refernces