2-Deoxy-2,3-didehydro-N-glycoloylneuraminic acid

Base Information

• Chemical Name: 2-Deoxy-2,3-didehydro-N-glycoloylneuraminic acid
• CAS No.: 39937-91-2
• Molecular Formula: C11H17NO9
• Molecular Weight: 307.254
• DSSTox Substance ID: DTXSID30192987
• Nikkaji Number: J825.374I
• Wikidata: Q83065684
• Mol file: 39937-91-2.mol

Synonyms:2-deoxy-2,3-didehydro-N-glycoloylneuraminic acid;DODH-NGNA

Chemical Property of 2-Deoxy-2,3-didehydro-N-glycoloylneuraminic acid

Chemical Property:

• Vapor Pressure: 5.47E-34mmHg at 25°C
• Boiling Point: 854.4°Cat760mmHg
• Flash Point: 470.5°C
• PSA: 180.27000
• Density: 1.69g/cm³
• LogP: -3.25390
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 307.09033112
• Heavy Atom Count: 21
• Complexity: 424

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(OC(C(C1O)NC(=O)CO)C(C(CO)O)O)C(=O)O
• Isomeric SMILES: C1=C(O[C@H]([C@@H]([C@H]1O)NC(=O)CO)[C@@H]([C@@H](CO)O)O)C(=O)O

Technology Process of 2-Deoxy-2,3-didehydro-N-glycoloylneuraminic acid

There total 9 articles about 2-Deoxy-2,3-didehydro-N-glycoloylneuraminic 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: 80.0%

ammonium 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate (1454818-68-8) + Acetoxyacetyl chloride (13831-31-7) → 2,6-anhydro-3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-D-galacto-non-2-enoic acid (39937-91-2)

Guidance literature:

ammonium 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate; Acetoxyacetyl chloride; With triethylamine; In 1,4-dioxane; water; at 0 - 40 ℃; for 2h; Microwave irradiation; Sealed tube;

With methanol; sodium hydroxide; In water; at 0 - 20 ℃; for 1h; Microwave irradiation; Sealed tube;

In water; Microwave irradiation; Sealed tube;

DOI:10.1016/j.tetlet.2013.07.107

Reference yield: 74.8%

5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid (41976-42-5) + Acetoxyacetyl chloride (13831-31-7) → 2,6-anhydro-3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-D-galacto-non-2-enoic acid (39937-91-2)

Guidance literature:

5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid; Acetoxyacetyl chloride; With potassium carbonate; In methanol; for 6h;

With sodium hydroxide; In water; for 1h; pH=10 - 11;

Reference yield:

5-acetoxyacetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enoinic acid → 2,6-anhydro-3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-D-galacto-non-2-enoic acid (39937-91-2)

Guidance literature:

With sodium hydroxide; water; at 20 ℃; for 2h;

DOI:10.1016/S0957-4166(99)00552-2

upstream raw materials:

5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

ammonium 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

Acetoxyacetyl chloride