6-O-allyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

Base Information

• Chemical Name: 6-O-allyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate
• CAS No.: 1448013-33-9
• Molecular Formula: C₅₈H₆₄N₆O₁₄
• Molecular Weight: 1069.18
• Mol file: 1448013-33-9.mol

Synonyms:

Chemical Property of 6-O-allyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-allyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

There total 14 articles about 6-O-allyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate 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:

O-benzyl-D-serine (10433-52-0,32520-12-0) → 6-O-allyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate (1448013-33-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium nitrite; sulfuric acid / water / 5 h / 0 - 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 24.5 h / 0 - 20 °C

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane; diethyl ether / 1 h / -20 - -10 °C / Molecular sieve

4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 1.5 h / 0 - 20 °C

5: trimethylsilyl trifluoromethanesulfonate / dichloromethane; diethyl ether / 1 h / -20 - -10 °C / Molecular sieve

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; In aq. phosphate buffer; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c3cc43545h

Reference yield:

3-(benzyloxy)-(R)-2-hydroxy-propionic acid (127744-27-8,130111-08-9) → 6-O-allyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate (1448013-33-9)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide / 24.5 h / 0 - 20 °C

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane; diethyl ether / 1 h / -20 - -10 °C / Molecular sieve

3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 1.5 h / 0 - 20 °C

4: trimethylsilyl trifluoromethanesulfonate / dichloromethane; diethyl ether / 1 h / -20 - -10 °C / Molecular sieve

With trimethylsilyl trifluoromethanesulfonate; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In aq. phosphate buffer; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c3cc43545h

Reference yield:

benzyl (2R)-2-hydroxy-3-benzyloxypropanoate → 6-O-allyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate (1448013-33-9)

Guidance literature:

Multi-step reaction with 3 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; diethyl ether / 1 h / -20 - -10 °C / Molecular sieve

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 1.5 h / 0 - 20 °C

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane; diethyl ether / 1 h / -20 - -10 °C / Molecular sieve

With trimethylsilyl trifluoromethanesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In aq. phosphate buffer; diethyl ether; dichloromethane;

DOI:10.1039/c3cc43545h

upstream raw materials:

O-benzyl-D-serine

3-(benzyloxy)-(R)-2-hydroxy-propionic acid

2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

2-azido-4,6-O-benzylidene-1-O-tert-butyldimethylsilyl-2-deoxy-3-O-(2-naphthalenylmethyl)-D-glucopyranoside

Downstream raw materials:

2-N-acetyl-6-O-allyl-3,4-di-O-benzyl-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-O-levulinoyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

2-N-acetyl-3,4-di-O-benzyl-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate