(2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl ester

Base Information

• Chemical Name: (2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl ester
• CAS No.: 868845-61-8
• Molecular Formula: C₃₉H₄₃N₃O₅
• Molecular Weight: 633.788

Synonyms:(2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl ester

Chemical Property of (2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl ester

Chemical Property:

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Technology Process of (2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl ester

There total 1 articles about (2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl 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: 32.0%

3-tert-butoxy-2-[3-(1H-indol-3-yl)-2-(trityl-amino)-propionylamino]-butyric acid methyl ester → (2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl ester (868845-61-8) + (2S,3R)-3-tert-Butoxy-2-[((2S,3aS,8aR)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl ester

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone; at -78 ℃; for 0.25h;

DOI:10.1021/jo051105t

Reference yield:

(2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl ester (868845-61-8) + triethylamine (121-44-8) → (2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid; compound with triethyl-amine

Guidance literature:

(2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl ester; With lithium hydroxide; water; In 1,4-dioxane; at 20 ℃; for 1h;

triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo051105t

Reference yield:

(2S,3R)-3-tert-Butoxy-2-[((2S,3aR,8aS)-3a-hydroxy-1-trityl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl)-amino]-butyric acid methyl ester (868845-61-8) → N1-trityl-3α-hydroxypyrrolo[2,3-b]indolyl-O-tbutyl-L-threonyl-S-trityl-L-cysteine methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiOH; H₂O / dioxane / 1 h / 20 °C

1.2: CH₂Cl₂; methanol

2.1: 0.03 g / DCC; HOBt; triethylamine / CH₂Cl₂ / 0 - 20 °C

With lithium hydroxide; water; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jo051105t

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