2,4-Dihydroxy-6-methylbenzoic acid 3-hydroxy-5-methyl-4-[[(2R,3S)-2,3,4-trihydroxybutoxy]carbonyl]phenyl ester

Base Information

• Chemical Name: 2,4-Dihydroxy-6-methylbenzoic acid 3-hydroxy-5-methyl-4-[[(2R,3S)-2,3,4-trihydroxybutoxy]carbonyl]phenyl ester
• CAS No.: 480-57-9
• Molecular Formula: C20H22O10
• Molecular Weight: 422.389
• Mol file: 480-57-9.mol

Synonyms:Erythrin;

Chemical Property of 2,4-Dihydroxy-6-methylbenzoic acid 3-hydroxy-5-methyl-4-[[(2R,3S)-2,3,4-trihydroxybutoxy]carbonyl]phenyl ester

Chemical Property:

• PSA: 173.98000
• LogP: 0.51030

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,4-Dihydroxy-6-methylbenzoic acid 3-hydroxy-5-methyl-4-[[(2R,3S)-2,3,4-trihydroxybutoxy]carbonyl]phenyl ester

There total 7 articles about 2,4-Dihydroxy-6-methylbenzoic acid 3-hydroxy-5-methyl-4-[[(2R,3S)-2,3,4-trihydroxybutoxy]carbonyl]phenyl 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:

C34H34O10 → (2S,3R)-(-)-erythrin (480-57-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 6h;

DOI:10.1016/j.tetlet.2013.09.071

Reference yield:

3-hydroxy-5-methyl-4-(((2S,3R)-2,3,4-tris(benzyloxy)butoxy)carbonyl)phenyl 2,4-bis(benzyloxy)-6-methylbenzoate (1213257-98-7) → (2S,3R)-(-)-erythrin (480-57-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 6h; under 760.051 Torr; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.11.134

Reference yield:

benzyl bromide (100-39-0) → (2S,3R)-(-)-erythrin (480-57-9)

Guidance literature:

Multi-step reaction with 4 steps

1: silver(l) oxide / diethyl ether / 72 h / 20 °C / Inert atmosphere; Darkness

2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice

3: sodium / toluene / 2 h / 11 °C

4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h

With lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; sodium; silver(l) oxide; In tetrahydrofuran; diethyl ether; ethyl acetate; toluene;

DOI:10.1016/j.tetlet.2013.09.071

upstream raw materials:

3-hydroxy-5-methyl-4-(((2S,3R)-2,3,4-tris(benzyloxy)butoxy)carbonyl)phenyl 2,4-bis(benzyloxy)-6-methylbenzoate

benzyl-2,4-bis(benzyloxy)-6-methylbenzoate

orsellinic acid

2,4-bis-(benzyloxy)-6-methylbenzoic acid

Downstream raw materials:

C₂₀H₂₂O₁₀

optically active 6-acetoxy-4-(4.6-diacetoxy-2-methyl-benzoyloxy)-2-methyl-benzoic acid-(erythro-2.3.4-triacetoxy-butyl ester)

(+)-montagnetol

Refernces

• 1、 Basset, Jean-Fran?ois,Leslie, Colin,Hamprecht, Dieter,White, Andrew J.P.,Barrett, Anthony G.M.. "Studies on the resorcylates: biomimetic total syntheses of (+)-montagnetol and (+)-erythrin". supporting information; experimental part. p. 783 - 785. Retrieved 2010/03/24.