5-azidopentyl (4-O-acetyl-3-O-allyl-6-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-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
• CAS No.: 419549-70-5
• Molecular Formula: C₅₈H₆₄N₄O₁₃
• Molecular Weight: 1025.17
• Mol file: 419549-70-5.mol

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

There total 10 articles about 5-azidopentyl (4-O-acetyl-3-O-allyl-6-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: 78.0%

ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-64-7) + 5-azidopentyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside (419549-61-4) → 5-azidopentyl (4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside (419549-70-5)

Guidance literature:

With 4 A molecular sieve; methyl trifluoromethanesulfonate; In diethyl ether; at 0 ℃; for 12h;

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

Reference yield:

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-28-4) → 5-azidopentyl (4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside (419549-70-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / NaH / tetrahydrofuran

2: 85 percent / BH₃*Me₃N; 4 Angstroem molecular sieves; AlCl₃ / tetrahydrofuran / 6 h / 20 °C

3: 95 percent / pyridine / 2 h

4: 78 percent / MeOTf; 4 Angstroem molecular sieves / diethyl ether / 12 h / 0 °C

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium hydride; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether;

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-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside (419549-70-5)

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: 78 percent / MeOTf; 4 Angstroem molecular sieves / diethyl ether / 12 h / 0 °C

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

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

upstream raw materials:

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

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

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

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

Downstream raw materials:

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