methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 876345-19-6
• Molecular Formula: C₄₃H₅₀O₉S
• Molecular Weight: 742.931

Synonyms:methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property of methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 2 articles about methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-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: 63.0%

3-O-acetyl-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranosyl chloride (111373-96-7) + methyl 2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside → methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (876345-19-6)

Guidance literature:

With 2,6-di-t-Bu-Me-pyridine; silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2005.10.056

Reference yield:

methyl 3-O-acetyl-2,4-di-O-benzyl-6-deoxy-1-thio-α-L-mannopyranoside → methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (876345-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / Cl₂ / CH₂Cl₂ / 0.08 h / 20 °C

2: 63 percent / AgOTf; 2,6-di-t-Bu-Me-pyridine / CH₂Cl₂ / 1 h / 20 °C

With 2,6-di-t-Bu-Me-pyridine; silver trifluoromethanesulfonate; chlorine; In dichloromethane;

DOI:10.1016/j.bmcl.2005.10.056

Reference yield: 94.0%

5-(methoxycarbonyl)pentyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (876345-18-5) + methyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (876345-19-6) → 5-methoxycarbonylpentyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (876345-20-9)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2005.10.056

upstream raw materials:

3-O-acetyl-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranosyl chloride

Downstream raw materials:

5-methoxycarbonylpentyl 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

5-methoxycarbonylpentyl 2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

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