2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucononitrile

Base Information

• Chemical Name: 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucononitrile
• CAS No.: 140183-55-7
• Molecular Formula: C₂₄H₂₆N₄O₉S
• Molecular Weight: 546.558
• Mol file: 140183-55-7.mol

Synonyms:2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucononitrile

Chemical Property of 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucononitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucononitrile

There total 9 articles about 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucononitrile 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: 58.0%

2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime (140183-54-6) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucononitrile (140183-55-7)

Guidance literature:

In dichloromethane; for 6h; Ambient temperature;

Reference yield:

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate (35946-66-8) → 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucononitrile (140183-55-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / (NH₄)2CO₃ / methanol; tetrahydrofuran

2: 74 percent / NH₂OH*HCl, pyridine / methanol

3: 58 percent / CH₂Cl₂

With pyridine; hydroxylamine hydrochloride; ammonium carbonate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)77717-3

Reference yield:

D-glucosamine hydrochloride (14131-63-6) → 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucononitrile (140183-55-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / NaHCO₃ / H₂O

2: 82 percent / Et₃N, DMAP / tetrahydrofuran

3: 88 percent / (NH₄)2CO₃ / methanol; tetrahydrofuran

4: 74 percent / NH₂OH*HCl, pyridine / methanol

5: 58 percent / CH₂Cl₂

With pyridine; dmap; hydroxylamine hydrochloride; ammonium carbonate; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/S0040-4039(00)77717-3

upstream raw materials:

2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime

1,1'-Thiocarbonyldiimidazole

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(benzyloxycarbonyl)amino-α/β-D-glucopyranoside

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

Downstream raw materials:

2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranose O-benzyl oxime ether

(3aS,4R,5R,6S,6aS)-6-(Acetoxymethyl)-2-oxohexahydro-2H-cyclopenta[d]oxazole-4,5-diyl diacetate

3,4,6-tri-O-acetylallosamizoline

(-)-allosamizoline hydrochloride