(S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxy-6,8-diiodo-isoquinoline-3-carboxylic acid

Base Information

• Chemical Name: (S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxy-6,8-diiodo-isoquinoline-3-carboxylic acid
• CAS No.: 271247-88-2
• Molecular Formula: C₁₈H₁₅I₂NO₅
• Molecular Weight: 579.13

Synonyms:(S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxy-6,8-diiodo-isoquinoline-3-carboxylic acid

Chemical Property of (S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxy-6,8-diiodo-isoquinoline-3-carboxylic acid

Chemical Property:

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Technology Process of (S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxy-6,8-diiodo-isoquinoline-3-carboxylic acid

There total 3 articles about (S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxy-6,8-diiodo-isoquinoline-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: 98.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (S)-7-hydroxy-6,8-diiodo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride → (S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxy-6,8-diiodo-isoquinoline-3-carboxylic acid (271247-88-2)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

Reference yield: 79.0%

N-(benzyloxycarbonyl)succinimide (75315-63-8) + (S)-7-hydroxy-6,8-diiodo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride → (S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxy-6,8-diiodo-isoquinoline-3-carboxylic acid (271247-88-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1021/jo0105991

Reference yield:

3,5-diiodo-l-tyrosine (300-39-0) → (S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxy-6,8-diiodo-isoquinoline-3-carboxylic acid (271247-88-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / aq. HCl / 1,2-dimethoxy-ethane / 19 h / 60 - 75 °C

2: 79 percent / Et₃N / CH₂Cl₂ / 0 °C

With hydrogenchloride; triethylamine; In 1,2-dimethoxyethane; dichloromethane; 1: Pictet-Spengler condensation;

DOI:10.1021/jo0105991

upstream raw materials:

N-(Benzyloxycarbonyloxy)succinimide

N-(benzyloxycarbonyl)succinimide

3,5-diiodo-l-tyrosine

Downstream raw materials:

methyl N-Cbz-L-1,2,3,4-tetrahydro-7-methoxy-6,8-di-iodoisoquinoline-3-carboxylate

(S)-2-benzyloxycarbonyl-3-(N-phenylpiperazin-4-ylcarbonyl)-7-[1-(dimethylamino)naphthalene-5-ylsulfonyloxy]-1,2,3,4-tetrahydroisoquinoline

(S)-3-(N-phenylpiperazin-4-ylcarbonyl)-7-[1-(dimethylamino)naphthalen-5-ylsulfonyloxy]-1,2,3,4-tetrahydroisoquinoline

(S)-2-benzyloxycarbonyl-3-(N-phenylpiperazin-4-ylcarbonyl)-7-(8-quinolinylsulfonyloxy)-1,2,3,4-tetrahydroisoquinoline

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