3-Isoquinolinecarboxylic acid, 2-formyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(phenylmethoxy)methyl]-, methyl ester, (1R,3S)-

Base Information

• Chemical Name: 3-Isoquinolinecarboxylic acid, 2-formyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(phenylmethoxy)methyl]-, methyl ester, (1R,3S)-
• CAS No.: 880262-28-2
• Molecular Formula: C22H25NO6
• Molecular Weight: 399.444
• Mol file: 880262-28-2.mol

Synonyms:

Chemical Property of 3-Isoquinolinecarboxylic acid, 2-formyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(phenylmethoxy)methyl]-, methyl ester, (1R,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Isoquinolinecarboxylic acid, 2-formyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(phenylmethoxy)methyl]-, methyl ester, (1R,3S)-

There total 4 articles about 3-Isoquinolinecarboxylic acid, 2-formyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(phenylmethoxy)methyl]-, methyl ester, (1R,3S)- 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: 90.0%

(1R,3S)-1-Benzyloxymethyl-2-formyl-6,7-dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (880262-26-0) + dimethyl sulfate (77-78-1) → (1R,3S)-1-Benzyloxymethyl-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (880262-28-2)

Guidance literature:

With potassium carbonate; In acetone; Heating;

DOI:10.1016/j.bmcl.2005.11.069

Reference yield:

(1R,3S)-1-Benzyloxymethyl-6,7-dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (880262-24-8) → (1R,3S)-1-Benzyloxymethyl-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (880262-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / acetic anhydride / 4 h

2: 90 percent / K₂CO₃ / acetone / Heating

With acetic anhydride; potassium carbonate; In acetone;

DOI:10.1016/j.bmcl.2005.11.069

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → (1R,3S)-1-Benzyloxymethyl-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (880262-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOAc / acetic acid / 20 h / 20 °C

2: 87 percent / acetic anhydride / 4 h

3: 90 percent / K₂CO₃ / acetone / Heating

With sodium acetate; acetic anhydride; potassium carbonate; In acetic acid; acetone; 1: Pictet-Spengler reaction;

DOI:10.1016/j.bmcl.2005.11.069

upstream raw materials:

(1R,3S)-1-Benzyloxymethyl-2-formyl-6,7-dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester

dimethyl sulfate

(1R,3S)-1-Benzyloxymethyl-6,7-dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester

benzyloxyacetoaldehyde

Downstream raw materials:

((1R,3S)-1-Benzyloxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-3-yl)-methanol

C₃₁H₃₄N₂O₆

C₃₂H₃₆N₂O₆

[2-(1-benzyloxymethyl-3-hydroxymethyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-1-(3,4-dimethoxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester