methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 105213-62-5
• Molecular Formula: C₇₂H₈₇NO₂₄
• Molecular Weight: 1350.48

Synonyms:methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property of methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

There total 13 articles about methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside 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: 88.0%

methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (247092-79-1) → methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (105213-62-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); N,N-dimethyl acetamide; tri-n-butyl-tin hydride; In toluene; at 90 ℃; for 1h;

DOI:10.1080/07328309908544033

Reference yield:

methyl 4-O-benzyl-α-L-rhamnopyranoside (25019-69-6) → methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (105213-62-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 36 percent / Et₃NI / CH₂Cl₂ / 96 h

2.1: 96 percent / TMSOTf / diethyl ether / 15 h / -78 - 20 °C

3.1: 98 percent / MeONa / CH₂Cl₂; methanol / 48 h / 20 °C

4.1: TMSOTf / acetonitrile / 0 - 20 °C / 89 Torr

5.1: H₂ / 1,5-COD-bis(trimethylphosphine)iridium hexafluorophosphate / tetrahydrofuran / 17 h

6.1: HgO; HgCl₂ / acetone; H₂O / 5 h / 20 °C

7.1: 98 percent / pyridine / 48 h

8.1: 88 percent / Bu₃SnH; N,N-dimethylacetamide; AIBN / toluene / 1 h / 90 °C

With pyridine; 2,2'-azobis(isobutyronitrile); N,N-dimethyl acetamide; trimethylsilyl trifluoromethanesulfonate; hydrogen; tri-n-butyl-tin hydride; sodium methylate; di(n-butyl)tin oxide; mercury dichloride; mercury(II) oxide; 1,5-COD-bis(trimethylphosphine)iridium hexafluorophosphate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene; acetonitrile; 1.1: Metallation / 1.2: Substitution / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Substitution / 5.1: Isomerization / 6.1: Substitution / 7.1: Acetylation / 8.1: Dehalogenation;

DOI:10.1080/07328309908544033

Reference yield:

2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide (67773-43-7) → methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (105213-62-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 36 percent / Et₃NI / CH₂Cl₂ / 96 h

2.1: 96 percent / TMSOTf / diethyl ether / 15 h / -78 - 20 °C

3.1: 98 percent / MeONa / CH₂Cl₂; methanol / 48 h / 20 °C

4.1: TMSOTf / acetonitrile / 0 - 20 °C / 89 Torr

5.1: H₂ / 1,5-COD-bis(trimethylphosphine)iridium hexafluorophosphate / tetrahydrofuran / 17 h

6.1: HgO; HgCl₂ / acetone; H₂O / 5 h / 20 °C

7.1: 98 percent / pyridine / 48 h

8.1: 88 percent / Bu₃SnH; N,N-dimethylacetamide; AIBN / toluene / 1 h / 90 °C

With pyridine; 2,2'-azobis(isobutyronitrile); N,N-dimethyl acetamide; trimethylsilyl trifluoromethanesulfonate; hydrogen; tri-n-butyl-tin hydride; sodium methylate; di(n-butyl)tin oxide; mercury dichloride; mercury(II) oxide; 1,5-COD-bis(trimethylphosphine)iridium hexafluorophosphate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene; acetonitrile; 1.1: Metallation / 1.2: Substitution / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Substitution / 5.1: Isomerization / 6.1: Substitution / 7.1: Acetylation / 8.1: Dehalogenation;

DOI:10.1080/07328309908544033

upstream raw materials:

methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide

methyl 4-O-benzyl-α-L-rhamnopyranoside

methyl [2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

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