Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ⁴-furo[3,2-d][1,3,2]dioxathiin-7-yl ester

Base Information

• Chemical Name: Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ⁴-furo[3,2-d][1,3,2]dioxathiin-7-yl ester
• CAS No.: 669055-55-4
• Molecular Formula: C₁₈H₁₈N₆O₆S
• Molecular Weight: 446.444
• Mol file: 669055-55-4.mol

Synonyms:Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ⁴-furo[3,2-d][1,3,2]dioxathiin-7-yl ester

Chemical Property of Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ⁴-furo[3,2-d][1,3,2]dioxathiin-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ⁴-furo[3,2-d][1,3,2]dioxathiin-7-yl ester

There total 2 articles about Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ⁴-furo[3,2-d][1,3,2]dioxathiin-7-yl 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: 94.0%

benzyl isothiocyanate (3173-56-6) + 9-(3,5-O-sulfinyl-β-D-xylofuranosyl)adenine (669055-53-2) → Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ4-furo[3,2-d][1,3,2]dioxathiin-7-yl ester (669055-55-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; acetonitrile; at 20 ℃;

DOI:10.1016/j.tetlet.2003.10.092

Reference yield:

adenine xyloside (524-69-6) → Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ4-furo[3,2-d][1,3,2]dioxathiin-7-yl ester (669055-55-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / SOCl₂; pyridine / acetonitrile

2: 94 percent / Et₃N / tetrahydrofuran; acetonitrile / 20 °C

With pyridine; thionyl chloride; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tetlet.2003.10.092

Reference yield: 60.0%

Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ4-furo[3,2-d][1,3,2]dioxathiin-7-yl ester (669055-55-4) → 9-(2,3-anhydro-β-D-ribofuranosyl)adenine (2627-64-7) + 9-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]adenine (125084-71-1)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; for 264h;

DOI:10.1016/j.tetlet.2003.10.092

upstream raw materials:

benzyl isothiocyanate

9-(3,5-O-sulfinyl-β-D-xylofuranosyl)adenine

adenine xyloside

Downstream raw materials:

9-(2,3-anhydro-β-D-ribofuranosyl)adenine

9-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]adenine

9-[3-(benzylamino)-3-deoxy-β-D-ribofuranosyl]adenine

3'-amino-3'-deoxyadenosine

Refernces