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

Base Information

• Chemical Name: 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
• CAS No.: 384371-55-5
• Molecular Formula: C₅₅H₅₄Cl₃NO₂₂
• Molecular Weight: 1187.39

Synonyms:

Chemical Property of 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

Chemical Property:

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Useful:

Technology Process of 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

There total 7 articles about 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 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:

allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (100639-25-6,71695-57-3) → 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-rhamnopyranosyl 2,2,2-trichloroacetimidate (384371-55-5)

Guidance literature:

Multi-step reaction with 6 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

5: aq. AcONa; AcOH / PdCl₂ / 16 h / 20 °C

6: 842 mg / DBU / CH₂Cl₂ / 3 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium dichloride; In dichloromethane;

Reference yield:

2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate (251451-05-5) → 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-rhamnopyranosyl 2,2,2-trichloroacetimidate (384371-55-5)

Guidance literature:

Multi-step reaction with 6 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

5: aq. AcONa; AcOH / PdCl₂ / 16 h / 20 °C

6: 842 mg / DBU / CH₂Cl₂ / 3 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium dichloride; In dichloromethane;

Reference yield:

Allyl 2',3',5'-tri-O-benzoyl-α-L-arabinofuranosyl-(1->4)-2-O-benzoyl-α-L-rhamnopyranoside (384371-52-2) → 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-rhamnopyranosyl 2,2,2-trichloroacetimidate (384371-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / TMSOTf / CH₂Cl₂ / 2 h / 0 °C

2: aq. AcONa; AcOH / PdCl₂ / 16 h / 20 °C

3: 842 mg / DBU / CH₂Cl₂ / 3 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In dichloromethane;

upstream raw materials:

trichloroacetonitrile

C₅₃H₅₄O₂₂

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

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

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