5,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-3-{{2,3,4-tri-O-acetyl-6-O-[4-O-acetyl-6-deoxy-2,3-O-(phenylmethylene)-α-L-mannopyranosyl]-β-D-glucopyranosyl}oxy}-4H-1-benzopyran-4-one

Base Information

• Chemical Name: 5,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-3-{{2,3,4-tri-O-acetyl-6-O-[4-O-acetyl-6-deoxy-2,3-O-(phenylmethylene)-α-L-mannopyranosyl]-β-D-glucopyranosyl}oxy}-4H-1-benzopyran-4-one
• CAS No.: 267005-98-1
• Molecular Formula: C₅₀H₅₀O₂₄
• Molecular Weight: 1034.93

Synonyms:5,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-3-{{2,3,4-tri-O-acetyl-6-O-[4-O-acetyl-6-deoxy-2,3-O-(phenylmethylene)-α-L-mannopyranosyl]-β-D-glucopyranosyl}oxy}-4H-1-benzopyran-4-one

Chemical Property of 5,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-3-{{2,3,4-tri-O-acetyl-6-O-[4-O-acetyl-6-deoxy-2,3-O-(phenylmethylene)-α-L-mannopyranosyl]-β-D-glucopyranosyl}oxy}-4H-1-benzopyran-4-one

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Technology Process of 5,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-3-{{2,3,4-tri-O-acetyl-6-O-[4-O-acetyl-6-deoxy-2,3-O-(phenylmethylene)-α-L-mannopyranosyl]-β-D-glucopyranosyl}oxy}-4H-1-benzopyran-4-one

There total 1 articles about 5,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-3-{{2,3,4-tri-O-acetyl-6-O-[4-O-acetyl-6-deoxy-2,3-O-(phenylmethylene)-α-L-mannopyranosyl]-β-D-glucopyranosyl}oxy}-4H-1-benzopyran-4-one 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:

acetic anhydride (108-24-7) + rutin benzylidene acetal → 5,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-3-{{2,3,4-tri-O-acetyl-6-O-[4-O-acetyl-6-deoxy-2,3-O-(phenylmethylene)-α-L-mannopyranosyl]-β-D-glucopyranosyl}oxy}-4H-1-benzopyran-4-one (267005-98-1)

Guidance literature:

With pyridine; dmap;

DOI:10.1002/(SICI)1522-2675(20000216)83:2<428::AID-HLCA428>3.0.CO;2-J

Reference yield: 76.0%

5,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-3-{{2,3,4-tri-O-acetyl-6-O-[4-O-acetyl-6-deoxy-2,3-O-(phenylmethylene)-α-L-mannopyranosyl]-β-D-glucopyranosyl}oxy}-4H-1-benzopyran-4-one (267005-98-1) + dibenzoyl peroxide (94-36-0) → 5,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-3-{[2,3,4-tri-O-acetyl-6-O-(4-O-acetyl-2-O-benzoyl-6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy}-4H-1-benzopyran-4-one

Guidance literature:

With N-Bromosuccinimide; water; barium carbonate; In chloroform; for 4h; Heating;

DOI:10.1002/(SICI)1522-2675(20000216)83:2<428::AID-HLCA428>3.0.CO;2-J

Reference yield:

5,7-bis(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-3-{{2,3,4-tri-O-acetyl-6-O-[4-O-acetyl-6-deoxy-2,3-O-(phenylmethylene)-α-L-mannopyranosyl]-β-D-glucopyranosyl}oxy}-4H-1-benzopyran-4-one (267005-98-1) → 3-{[6-O-(6-deoxy-3-O-sulfo-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one sodium salt

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / NBS; BaCO₃; H₂O / CHCl₃ / 4 h / Heating

2: SO₃*pyridine / dimethylformamide / 12 h / 50 °C

3: 100 mg / MeONa / methanol / 12 h

With N-Bromosuccinimide; pyridine-SO₃ complex; water; sodium methylate; barium carbonate; In methanol; chloroform; N,N-dimethyl-formamide; 1: Oxidation / 2: Addition / 3: Deacetylation;

DOI:10.1002/(SICI)1522-2675(20000216)83:2<428::AID-HLCA428>3.0.CO;2-J

upstream raw materials:

acetic anhydride

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