N⁶-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine

Base Information

• Chemical Name: N⁶-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine
• CAS No.: 932740-12-0
• Molecular Formula: C₃₁H₄₃N₇O₆
• Molecular Weight: 609.726

Synonyms:N⁶-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine

Chemical Property of N⁶-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine

There total 5 articles about N⁶-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine 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: 81.0%

6-chloro-6-deoxy-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyinosine (103201-21-4) + N1-benzyloxycarbonyl-1,8-octanediamine hydrochloride → N6-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine (932740-12-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; for 18h; Heating;

DOI:10.1021/jm061279i

Reference yield:

2',3'-O-isopropylideneinosine (2140-11-6) → N6-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine (932740-12-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy free radical; iodosobenzene diacetate / acetonitrile; H₂O / 4 h / 20 °C

2: SOCl₂; DMF / CHCl₃ / 5 h / Heating

3: 941 mg / tetrahydrofuran / 0.5 h / 5 - 20 °C

4: 81 percent / diisopropylethylamine / ethanol / 18 h / Heating

With thionyl chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; ethanol; chloroform; water; acetonitrile;

DOI:10.1021/jm061279i

Reference yield:

1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride (104940-65-0) → N6-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine (932740-12-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 941 mg / tetrahydrofuran / 0.5 h / 5 - 20 °C

2: 81 percent / diisopropylethylamine / ethanol / 18 h / Heating

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol;

DOI:10.1021/jm061279i

upstream raw materials:

6-chloro-6-deoxy-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyinosine

2',3'-O-isopropylideneinosine

1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride

Inosine

Downstream raw materials:

N⁶-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-5'-oxo-5'-deoxyadenosine

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