5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside

Base Information

• Chemical Name: 5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
• CAS No.: 419549-76-1
• Molecular Formula: C₆₂H₆₆N₄O₁₃
• Molecular Weight: 1075.23
• Mol file: 419549-76-1.mol

Synonyms:5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside

Chemical Property of 5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside

There total 7 articles about 5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 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: 83.0%

ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (138730-66-2) + 5-azidopentyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside (419549-61-4) → 5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside (419549-76-1)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -15 ℃;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

Reference yield:

ethyl 2,6-di-O-benzyl-1-thio-β-D-galactopyranoside (215371-44-1) → 5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside (419549-76-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 76 percent / p-TsOH*H₂O / 0.1 h

2.1: 77 percent / LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 0.33 h

3.1: 96 percent / pyridine / 2 h

4.1: 89 percent / MeOTf; 4 Angstroem molecular sieves / diethyl ether / 5 h / 0 °C

5.1: NaOMe / methanol; CH₂Cl₂ / 1 h

5.2: 30 percent / TiCl₄; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h

6.1: 83 percent / AgOTf; N-iodosuccinimide; 4 Angstroem molecular sieves / acetonitrile; CH₂Cl₂ / -15 °C

With pyridine; N-iodo-succinimide; lithium aluminium tetrahydride; aluminium trichloride; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; methyl trifluoromethanesulfonate; In methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

Reference yield:

ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (213459-71-3) → 5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside (419549-76-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 96 percent / aq. AcOH / 1 h / 60 °C

2.1: 76 percent / p-TsOH*H₂O / 0.1 h

3.1: 77 percent / LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 0.33 h

4.1: 96 percent / pyridine / 2 h

5.1: 89 percent / MeOTf; 4 Angstroem molecular sieves / diethyl ether / 5 h / 0 °C

6.1: NaOMe / methanol; CH₂Cl₂ / 1 h

6.2: 30 percent / TiCl₄; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h

7.1: 83 percent / AgOTf; N-iodosuccinimide; 4 Angstroem molecular sieves / acetonitrile; CH₂Cl₂ / -15 °C

With pyridine; N-iodo-succinimide; lithium aluminium tetrahydride; aluminium trichloride; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; methyl trifluoromethanesulfonate; In methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

upstream raw materials:

ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

5-azidopentyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside

ethyl 2,6-di-O-benzyl-1-thio-β-D-galactopyranoside

ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Downstream raw materials:

5-azidopentyl (3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside