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
Hs Code.:

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

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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

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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%

: 138730-66-2
ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 419549-61-4
5-azidopentyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside

: 419549-76-1
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

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:

: 215371-44-1
ethyl 2,6-di-O-benzyl-1-thio-β-D-galactopyranoside

: 419549-76-1
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

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:

: 213459-71-3
ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

: 419549-76-1
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

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