isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside
• CAS No.: 1269649-17-3
• Molecular Formula: C₂₈H₃₈O₁₂S
• Molecular Weight: 598.669

Synonyms:isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

Chemical Property of isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

There total 3 articles about isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-1-thio-β-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: 91.0%

isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (1269649-14-0) → isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (1269649-17-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2010.12.046

Reference yield:

isopropyl 3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (615570-26-8) → isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (1269649-17-3)

Guidance literature:

Multi-step reaction with 2 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.75 h / 0 °C / Inert atmosphere

2: triethylamine / dichloromethane / 3 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2010.12.046

Reference yield:

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (113893-72-4) → isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (1269649-17-3)

Guidance literature:

Multi-step reaction with 2 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.75 h / 0 °C / Inert atmosphere

2: triethylamine / dichloromethane / 3 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2010.12.046

upstream raw materials:

isopropyl 3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

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

Downstream raw materials:

isopropyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->3)-[2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)]-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

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