methyl 5-acetamido-8,9-O-benzylidene-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Base Information

• Chemical Name: methyl 5-acetamido-8,9-O-benzylidene-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate
• CAS No.: 133585-58-7
• Molecular Formula: C₁₉H₂₃NO₈
• Molecular Weight: 393.394
• Mol file: 133585-58-7.mol

Synonyms:methyl 5-acetamido-8,9-O-benzylidene-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Chemical Property of methyl 5-acetamido-8,9-O-benzylidene-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-acetamido-8,9-O-benzylidene-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

There total 1 articles about methyl 5-acetamido-8,9-O-benzylidene-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 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: 85.0%

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate (25875-99-4,79026-38-3) + benzaldehyde dimethyl acetal (1125-88-8) → methyl 5-acetamido-8,9-O-benzylidene-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (133585-58-7)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; for 3h; Ambient temperature;

DOI:10.1021/jo00032a601

Reference yield:

methyl 5-acetamido-8,9-O-benzylidene-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (133585-58-7) → methyl 5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (123170-14-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) CaH₂, Bu₄NI, KOH / 1a) THF, DMSO, 0 deg C, 4h, 1b) RT, 16h, 2) ether

2: 83 percent / BH₃*NMe₃, AlCl₃, molecular sieve 4A / tetrahydrofuran / 1) 0 deg C, 0.5h, 2) RT, 2h

With potassium hydroxide; aluminium trichloride; calcium hydride; trimethylamine-borane; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran;

DOI:10.1021/jo00032a601

Reference yield:

methyl 5-acetamido-8,9-O-benzylidene-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (133585-58-7) → methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (123170-15-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) CaH₂, Bu₄NI, KOH / 1a) THF, DMSO, 0 deg C, 4h, 1b) RT, 16h, 2) ether

2: 83 percent / BH₃*NMe₃, AlCl₃, molecular sieve 4A / tetrahydrofuran / 1) 0 deg C, 0.5h, 2) RT, 2h

3: 64 percent / Hg(CN)2, HgBr₂, molecular sieve 4A / CCl₄ / 1) -20 deg C, 0.5h, 2) 0 deg C, 1h, 3) RT, 18h

With potassium hydroxide; aluminium trichloride; calcium hydride; trimethylamine-borane; 4 A molecular sieve; mercury(II) cyanide; tetra-(n-butyl)ammonium iodide; mercury dibromide; In tetrahydrofuran; tetrachloromethane;

DOI:10.1021/jo00032a601

upstream raw materials:

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

benzaldehyde dimethyl acetal

Downstream raw materials:

methyl 5-acetamido-4,7-di-O-benzyl-8,9-O-benzylidene-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

methyl 5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

methyl O--(2->8)-5-acetamido-4,7,9-tri-O-benzyl-2,3-didehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate