(+)-3,4,5-Trihydroxybenzoic acid (2S,3R)-3,4-dihydro-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester

Base Information

• Chemical Name: (+)-3,4,5-Trihydroxybenzoic acid (2S,3R)-3,4-dihydro-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester
• CAS No.: 17445-91-9
• Molecular Formula: C₂₂H₁₈O₁₀
• Molecular Weight: 442.379
• Mol file: 17445-91-9.mol

Synonyms:(+)-3,4,5-Trihydroxybenzoic acid (2S,3R)-3,4-dihydro-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester;(+)-Robidanol 3-gallate

Chemical Property of (+)-3,4,5-Trihydroxybenzoic acid (2S,3R)-3,4-dihydro-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-3,4,5-Trihydroxybenzoic acid (2S,3R)-3,4-dihydro-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester

There total 6 articles about (+)-3,4,5-Trihydroxybenzoic acid (2S,3R)-3,4-dihydro-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester 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:

3,4,5-Tris-benzyloxy-benzoic acid (2S,3R)-7-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-yl ester → (+/-)-robidanol 3-O-gallate (17445-91-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1007/s00018-005-5422-7

Reference yield:

7-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-ol (896121-47-4) → (+/-)-robidanol 3-O-gallate (17445-91-9)

Guidance literature:

Multi-step reaction with 2 steps

1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆; 4-dimethylaminopyridine; 4-methylmorpholine / dimethylformamide

2: H₂ / Pd/C / tetrahydrofuran; methanol

With 4-methyl-morpholine; dmap; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1007/s00018-005-5422-7

Reference yield:

7-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-2H-chromene (896121-42-9) → (+/-)-robidanol 3-O-gallate (17445-91-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BH₃*THF

1.2: aq. H₂O₂; NaOH

2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆; 4-dimethylaminopyridine; 4-methylmorpholine / dimethylformamide

3.1: H₂ / Pd/C / tetrahydrofuran; methanol

With 4-methyl-morpholine; dmap; borane-THF; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1007/s00018-005-5422-7

upstream raw materials:

7-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-2H-chromene

7-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-ol

1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone

3,4,5-tribenzyloxybenzaldehyde

Downstream raw materials:

(2R,3S)-2,3-trans-3-O-(3,4,5-trimethoxygalloyl)-3',4',5',7-tetramethoxyflavan