5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid

Base Information

• Chemical Name: 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid
• CAS No.: 125288-69-9
• Molecular Formula: C₃₉H₄₁NO₈
• Molecular Weight: 651.756
• Mol file: 125288-69-9.mol

Synonyms:5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid

Chemical Property of 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid

There total 3 articles about 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-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:

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) → 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (125288-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol

2: KOH, BaO, Bu₄NI / dimethylsulfoxide

With potassium hydroxide; sodium methylate; tetra-(n-butyl)ammonium iodide; barium(II) oxide; In methanol; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)61852-X

Reference yield:

2,3-dehydro-2-deoxy-N-acetylneuraminic acid (24967-27-9,79026-37-2,108675-60-1,108675-61-2,108675-62-3) + benzyl bromide (100-39-0) → 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (125288-69-9)

Guidance literature:

With potassium hydroxide; tetra-(n-butyl)ammonium iodide; barium(II) oxide; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)61852-X

Reference yield:

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) + benzyl bromide (100-39-0) → 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (125288-69-9)

Guidance literature:

With potassium hydroxide; sodium methylate; tetra-(n-butyl)ammonium iodide; barium(II) oxide; Yield given. Multistep reaction; 1)MeOH, room temp., 3h, 2)DMSO, room temp., 18h;

DOI:10.1016/S0040-4020(01)97586-6

upstream raw materials:

2,3-dehydro-2-deoxy-N-acetylneuraminic acid

benzyl bromide

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

Downstream raw materials:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

(3R,4R,5S,6R)-2-Acetoxy-5-acetylamino-4-benzyloxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose