3,4-di-O-acetyl-5-amino-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-N-benzyloxycarbonyl-1,5-dideoxy-5,6-N,O-isopropyliden-D-arabilo-hex-2-ulose

Base Information

• Chemical Name: 3,4-di-O-acetyl-5-amino-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-N-benzyloxycarbonyl-1,5-dideoxy-5,6-N,O-isopropyliden-D-arabilo-hex-2-ulose
• CAS No.: 408359-43-3
• Molecular Formula: C₅₅H₆₁NO₁₃
• Molecular Weight: 944.088
• Mol file: 408359-43-3.mol

Synonyms:

Chemical Property of 3,4-di-O-acetyl-5-amino-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-N-benzyloxycarbonyl-1,5-dideoxy-5,6-N,O-isopropyliden-D-arabilo-hex-2-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-acetyl-5-amino-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-N-benzyloxycarbonyl-1,5-dideoxy-5,6-N,O-isopropyliden-D-arabilo-hex-2-ulose

There total 4 articles about 3,4-di-O-acetyl-5-amino-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-N-benzyloxycarbonyl-1,5-dideoxy-5,6-N,O-isopropyliden-D-arabilo-hex-2-ulose 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: 55.0%

acetic anhydride (108-24-7) + (R)-4-[1,2-Dihydroxy-3-oxo-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (408359-26-2) → (R)-4-[(1S,2R)-1,2-Diacetoxy-3-oxo-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester + 3,4-di-O-acetyl-5-amino-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-N-benzyloxycarbonyl-1,5-dideoxy-5,6-N,O-isopropyliden-D-arabilo-hex-2-ulose (408359-43-3)

Guidance literature:

With pyridine; dmap; for 1.5h;

DOI:10.1081/CAR-100108281

Reference yield:

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (133464-37-6) → 3,4-di-O-acetyl-5-amino-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-N-benzyloxycarbonyl-1,5-dideoxy-5,6-N,O-isopropyliden-D-arabilo-hex-2-ulose (408359-43-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / acetonitrile / 120 h

2: 75 percent / N-methylmorpholine-N-oxide; OsO₄ / H₂O; acetone; 2-methyl-propan-2-ol / 4 h

3: 55 percent / pyridine; DMAP / 1.5 h

With pyridine; dmap; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1081/CAR-100108281

Reference yield:

2-oxo-3-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)propylidenetriphenylphosphorane (124667-94-3) → 3,4-di-O-acetyl-5-amino-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-N-benzyloxycarbonyl-1,5-dideoxy-5,6-N,O-isopropyliden-D-arabilo-hex-2-ulose (408359-43-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / acetonitrile / 120 h

2: 75 percent / N-methylmorpholine-N-oxide; OsO₄ / H₂O; acetone; 2-methyl-propan-2-ol / 4 h

3: 55 percent / pyridine; DMAP / 1.5 h

With pyridine; dmap; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1081/CAR-100108281

upstream raw materials:

acetic anhydride

(R)-4-[1,2-Dihydroxy-3-oxo-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

2-oxo-3-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)propylidenetriphenylphosphorane