Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-azido-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-azido-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 158008-50-5
• Molecular Formula: C₃₀H₄₀N₄O₁₅
• Molecular Weight: 696.665
• Mol file: 158008-50-5.mol

Synonyms:Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-azido-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-azido-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-azido-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

There total 6 articles about Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-azido-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester 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: 56.0%

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) + 2-acetamido-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-azido-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (158008-50-5)

Guidance literature:

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate; 2-acetamido-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide; In dichloromethane; toluene; at 20 ℃; for 2h; Inert atmosphere; Molecular sieve;

With boron trifluoride diethyl etherate; In dichloromethane; toluene; at -40 ℃; Inert atmosphere;

DOI:10.1002/chem.202004076

Reference yield: 55.0%

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-4-allyloxy-6-azido-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (158008-49-2) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-azido-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (158008-50-5)

Guidance literature:

With sodium acetate; palladium dichloride; In acetic acid; at 50 ℃;

Reference yield:

azido 4,6-O-(4-methoxybenzylidene)-2-deoxy-2-acetamido-β-D-glucopyranoside → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-azido-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (158008-50-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Ba(OH)2 / dimethylformamide

2: NaCNBH₃, CF₃COOH / dimethylformamide

3: 78 percent / AgOTf, 2,6-di-tert-butylpyridine / CH₂Cl₂; toluene

4: 55 percent / PdCl₂, NaOAc / acetic acid / 50 °C

With barium dihydroxide; 2,6-di-tert-butyl-pyridine; sodium acetate; silver trifluoromethanesulfonate; sodium cyanoborohydride; trifluoroacetic acid; palladium dichloride; In dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene;

upstream raw materials:

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-4-allyloxy-6-azido-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

N-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl]-acetamide

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

Downstream raw materials:

C₆₀H₇₄N₄O₂₂