2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone

Base Information

• Chemical Name: 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone
• CAS No.: 154125-83-4
• Molecular Formula: C₂₉H₃₂N₂O₆
• Molecular Weight: 504.583
• Mol file: 154125-83-4.mol

Synonyms:2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone

Chemical Property of 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone

There total 2 articles about 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone 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:

N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide (4171-79-3,121123-45-3,4171-72-6) → 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone (154125-83-4)

Guidance literature:

With sodium periodate; hydroxylamine hydrochloride; sodium acetate; sodium; Yield given. Multistep reaction; 1.) MeOH, EtOH, 60 deg C, 33 h; 2.) H₂O, EtOH, 17.75 h;

DOI:10.1002/hlca.19930760811

Reference yield:

allyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside (154172-26-6) → 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone (154125-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) KO(t-Bu); 2.) I₂ / 1.) DMSO, 50 deg C, 15 min; 2.) THF, H₂O, 26 deg C, 15 min

2: 1.) NH₂OH*HCl, Na; 2.) NaIO₄, NaOAc / 1.) MeOH, EtOH, 60 deg C, 33 h; 2.) H₂O, EtOH, 17.75 h

With sodium periodate; hydroxylamine hydrochloride; potassium tert-butylate; iodine; sodium acetate; sodium;

DOI:10.1002/hlca.19930760811

Reference yield: 100.0%

p-toluenesulfonyl chloride (98-59-9) + 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone (154125-83-4) → (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosylidene)amino 4-methylbenzene-1-sulfonate (154125-84-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1002/hlca.19930760811

upstream raw materials:

N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide

allyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside

Downstream raw materials:

(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosylidene)amino 4-methylbenzene-1-sulfonate

2-acetamido-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-hydrazi-D-glucitol

2-acetamido-1,5-anhydro-1-azi-3,4,6-tri-O-benzyl-2-deoxy-D-glucitol