2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-β-D-glucopyranoside
• CAS No.: 724764-05-0
• Molecular Formula: C₆₉H₈₂N₄O₂₃
• Molecular Weight: 1335.42

Synonyms:2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-β-D-glucopyranoside

Chemical Property of 2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-β-D-glucopyranoside

There total 9 articles about 2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-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: 95.0%

2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside (724764-04-9) → 2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-β-D-glucopyranoside (724764-05-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; at 0 ℃; for 1h;

DOI:10.1039/b400986j

Reference yield:

allyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranoside (497182-24-8) → 2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-β-D-glucopyranoside (724764-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₂ / [Ir(COD){PCH₃(C₆H₅)2}2](+)*PF₆(-) / tetrahydrofuran / 20 °C

1.2: 86 percent / HgO; HgCl₂ / acetone; H₂O / 2 h / 20 °C

2.1: 90 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 1 h / 20 °C

3.2: 76 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / 2 h / 0 - 65 °C

4.1: 95 percent / TFA / CH₂Cl₂; H₂O / 1 h / 0 °C

With 4 A molecular sieve; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1039/b400986j

Reference yield:

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (122089-71-8) → 2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-β-D-glucopyranoside (724764-05-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 89 percent / TMSOTf / diethyl ether / 2.5 h / -50 - 20 °C

2.1: H₂ / [Ir(COD){PCH₃(C₆H₅)2}2](+)*PF₆(-) / tetrahydrofuran / 20 °C

2.2: 86 percent / HgO; HgCl₂ / acetone; H₂O / 2 h / 20 °C

3.1: 90 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 1 h / 20 °C

4.2: 76 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / 2 h / 0 - 65 °C

5.1: 95 percent / TFA / CH₂Cl₂; H₂O / 1 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1039/b400986j

upstream raw materials:

2-azidoethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-4,6-isopropylidene-β-D-glucopyranoside

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

2'-azidoethyl 2-acetamido-2-deoxy-β-D-glucopyranoside

2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

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