(3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

Base Information

• Chemical Name: (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• CAS No.: 352015-85-1
• Molecular Formula: C₂₇H₂₆N₂O₅
• Molecular Weight: 458.514

Synonyms:(3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

Chemical Property of (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

There total 3 articles about (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 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: 75.0%

methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (352015-84-0) → (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (352015-85-1)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2008.05.022

Reference yield:

4-(benzyloxy)-3,5-dimethoxybenzaldehyde (6527-32-8) → (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (352015-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / toluene / 20 h / Heating

2: LiOH / tetrahydrofuran / Heating

With lithium hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran; toluene; 1: Pictet-Spengler reaction;

DOI:10.1016/S0960-894X(01)00136-6

Reference yield:

L-tryptophan methyl ester (4299-70-1) → (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (352015-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / toluene / 20 h / Heating

2: LiOH / tetrahydrofuran / Heating

With lithium hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran; toluene; 1: Pictet-Spengler reaction;

DOI:10.1016/S0960-894X(01)00136-6

upstream raw materials:

methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

4-(benzyloxy)-3,5-dimethoxybenzaldehyde

L-tryptophan methyl ester

Downstream raw materials:

{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-acetic acid methyl ester

(S)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-propionic acid methyl ester

(S)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-3-methyl-butyric acid methyl ester

(S)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-4-methyl-pentanoic acid methyl ester

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