ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-1-thio-β-D-glucopyranoside
• CAS No.: 927680-43-1
• Molecular Formula: C₂₀H₂₇N₃O₅S
• Molecular Weight: 421.517

Synonyms:ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-1-thio-β-D-glucopyranoside

There total 6 articles about ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-1-thio-β-D-glucopyranoside 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:

4-Oxo-pentanoic acid (2S,3R,4R,5S,6R)-4-benzyloxy-2-ethylsulfanyl-6-methyl-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester → ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-1-thio-β-D-glucopyranoside (927680-43-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 40 ℃;

DOI:10.1002/chem.200601245

Reference yield:

4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-ethylsulfanyl-4,5-dihydroxy-6-methyl-tetrahydro-pyran-3-yl ester (927680-56-6) → ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-1-thio-β-D-glucopyranoside (927680-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 52 percent / tetrabutylammonium bromide / toluene / 3 h / Heating

2.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: 0.42 g / sodium azide / dimethylformamide / 40 °C

With pyridine; sodium azide; di(n-butyl)tin oxide; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.200601245

Reference yield:

ethyl 3,4-O-isopropylidene-2-O-levulinoyl-1-thio-β-D-fucopyranoside (927680-41-9) → ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-1-thio-β-D-glucopyranoside (927680-43-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / aq. acetic acid / 0.25 h / 90 °C

2.1: dibutyltin oxide / toluene / 3 h / Heating

2.2: 52 percent / tetrabutylammonium bromide / toluene / 3 h / Heating

3.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

4.1: 0.42 g / sodium azide / dimethylformamide / 40 °C

With pyridine; sodium azide; di(n-butyl)tin oxide; acetic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.200601245

upstream raw materials:

4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-ethylsulfanyl-4,5-dihydroxy-6-methyl-tetrahydro-pyran-3-yl ester

ethyl 3,4-O-isopropylidene-2-O-levulinoyl-1-thio-β-D-fucopyranoside

ethyl 3-O-benzyl-2-O-levulinoyl-1-thio-β-D-fucopyranoside

levulinic acid

Downstream raw materials:

3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-acetamido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-azido-3-O-benzyl-4,6-dideoxy-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

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