Allyl 2^D,3^D,5^D-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-[2^C,3^C,4^C,6^C-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2^B-O-benzoyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: Allyl 2^D,3^D,5^D-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-[2^C,3^C,4^C,6^C-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2^B-O-benzoyl-α-L-rhamnopyranoside
• CAS No.: 384371-53-3
• Molecular Formula: C₅₆H₅₈O₂₂
• Molecular Weight: 1083.06

Synonyms:Allyl 2^D,3^D,5^D-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-[2^C,3^C,4^C,6^C-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2^B-O-benzoyl-α-L-rhamnopyranoside

Chemical Property of Allyl 2^D,3^D,5^D-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-[2^C,3^C,4^C,6^C-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2^B-O-benzoyl-α-L-rhamnopyranoside

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Technology Process of Allyl 2^D,3^D,5^D-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-[2^C,3^C,4^C,6^C-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2^B-O-benzoyl-α-L-rhamnopyranoside

There total 5 articles about Allyl 2^D,3^D,5^D-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-[2^C,3^C,4^C,6^C-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2^B-O-benzoyl-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: 78.0%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) + Allyl 2',3',5'-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-2-O-benzoyl-α-L-rhamnopyranoside (384371-52-2) → C56H58O22 + Allyl 2D,3D,5D-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-[2C,3C,4C,6C-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2B-O-benzoyl-α-L-rhamnopyranoside (384371-53-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 3.66667h;

Reference yield:

allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (100639-25-6,71695-57-3) → Allyl 2D,3D,5D-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-[2C,3C,4C,6C-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2B-O-benzoyl-α-L-rhamnopyranoside (384371-53-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / TMSOTf / CH₂Cl₂ / 2 h / 0 °C

2: aq. TFA / CH₂Cl₂ / 0.33 h / 20 °C

3: 3.7 g / pyridine / 6 h

4: 63 percent / TMSOTf / CH₂Cl₂ / 2 h / 0 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In dichloromethane;

Reference yield:

2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate (251451-05-5) → Allyl 2D,3D,5D-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-[2C,3C,4C,6C-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2B-O-benzoyl-α-L-rhamnopyranoside (384371-53-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / TMSOTf / CH₂Cl₂ / 2 h / 0 °C

2: aq. TFA / CH₂Cl₂ / 0.33 h / 20 °C

3: 3.7 g / pyridine / 6 h

4: 63 percent / TMSOTf / CH₂Cl₂ / 2 h / 0 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In dichloromethane;

upstream raw materials:

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

Allyl 2',3',5'-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-2-O-benzoyl-α-L-rhamnopyranoside

allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate

Downstream raw materials:

C₅₃H₅₄O₂₂

2^D,3^D,5^D-Tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-[2^C,3^C,4^C,6^C-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2^B-O-benzoyl-α-L-rhamnopyranosyl 2,2,2-trichloroacetimidate

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