(4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-ol

Base Information

• Chemical Name: (4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-ol
• CAS No.: 1373335-76-2
• Molecular Formula: C₂₁H₂₆N₆O₅S
• Molecular Weight: 474.541
• Mol file: 1373335-76-2.mol

Synonyms:(4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-ol

Chemical Property of (4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-ol

There total 5 articles about (4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-ol 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%

2-Methoxypropene (116-11-0) + (2S,3R,4R,5S)-2-(9-adeninylmethyl)-3,4-dihydroxy-5-(hydroxymethyl)-N-(p-toluenesulfonamido)pyrrolidine (1373335-75-1) → (4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-ol (1373335-76-2)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo3004452

Reference yield:

(2S,3R,4R,5S)-2-acetoxymethyl-3,4-di-O-benzyl-5-benzyloxymethyl-N-(p-toluenesulfonamido)pyrrolidine (881185-59-7) → (4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-ol (1373335-76-2)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium carbonate / methanol / 1.5 h / Reflux

2: pyridine / 50 °C

3: 18-crown-6 ether; potassium carbonate / N,N-dimethyl-formamide / 90 °C

4: hydrogenchloride / water / 2 h / Reflux

5: toluene-4-sulfonic acid / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; 18-crown-6 ether; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo3004452

Reference yield:

(2S,3R,4R,5S)-3,4-bis-(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)-N-(p-toluenesulfonamido)pyrrolidine (881185-65-5) → (4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-ol (1373335-76-2)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 50 °C

2: 18-crown-6 ether; potassium carbonate / N,N-dimethyl-formamide / 90 °C

3: hydrogenchloride / water / 2 h / Reflux

4: toluene-4-sulfonic acid / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; 18-crown-6 ether; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/jo3004452

upstream raw materials:

(2S,3R,4R,5S)-3,4-bis-(benzyloxy)-5-(benzyloxymethyl)-2-(hydroxymethyl)-N-(p-toluenesulfonamido)pyrrolidine

(2S,3R,4R,5S)-2-acetoxymethyl-3,4-di-O-benzyl-5-benzyloxymethyl-N-(p-toluenesulfonamido)pyrrolidine

2-Methoxypropene

(2S,3R,4R,5S)-2-(9-adeninylmethyl)-3,4-dihydroxy-5-(hydroxymethyl)-N-(p-toluenesulfonamido)pyrrolidine

Downstream raw materials:

(2S,3S,4R,5S)-2-(9-adenylmethyl)-(3-O,5-C-methylene)-N-(ptoluenesulfonamido)pyrrolidine

(4aS,6S,7R,7aR)-6-((6-amino-9H-purin-9-yl)methyl)-2,2-dimethyl-5-tosylhexahydro[1,3]dioxino[5,4-b]pyrrol-7-yl trifluoromethanesulfonate