N⁶-tert-butoxycarbonyl-5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine

Base Information

• Chemical Name: N⁶-tert-butoxycarbonyl-5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine
• CAS No.: 873556-36-6
• Molecular Formula: C₃₂H₃₆N₆O₁₀S
• Molecular Weight: 696.738

Synonyms:N⁶-tert-butoxycarbonyl-5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine

Chemical Property of N⁶-tert-butoxycarbonyl-5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-tert-butoxycarbonyl-5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine

There total 6 articles about N⁶-tert-butoxycarbonyl-5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine 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:

((3aR,4R,6R,6aR)-6-(6-((tert-butoxycarbonyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate (873556-35-5) + N-[(2-benzyloxyphenyl)carboxy]succinimide (287971-19-1) → N6-tert-butoxycarbonyl-5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine (873556-36-6)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jm051060o

Reference yield:

tert-butyl (9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate (686301-05-3) → N6-tert-butoxycarbonyl-5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine (873556-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / 1,2-dimethoxy-ethane / 0.5 h / 0 °C

1.2: 82 percent / NH₂SO₂Cl / 1,2-dimethoxy-ethane / 16 h / 20 °C

2.1: Cs₂CO₃ / dimethylformamide / 16 h / 20 °C

With sodium hydride; caesium carbonate; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/jm051060o

Reference yield:

tert-butyl (9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate (913823-87-7) → N6-tert-butoxycarbonyl-5'-O-(N-(2-benzyloxybenzoyl)sulfamoyl)-2',3'-O-isopropylideneadenosine (873556-36-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

2.1: NaH / 1,2-dimethoxy-ethane / 0.5 h / 0 °C

2.2: 82 percent / NH₂SO₂Cl / 1,2-dimethoxy-ethane / 16 h / 20 °C

3.1: Cs₂CO₃ / dimethylformamide / 16 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; caesium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/jm051060o

upstream raw materials:

((3aR,4R,6R,6aR)-6-(6-((tert-butoxycarbonyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate

N-[(2-benzyloxyphenyl)carboxy]succinimide

tert-butyl (9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate

tert-butyl (9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate

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