(-)-9-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine

Base Information

Chemical Name:(-)-9-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine
CAS No.:171721-10-1
Molecular Formula:C₃₁H₃₁N₅O₄
Molecular Weight:537.618
Hs Code.:

Synonyms:(-)-9-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine

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Chemical Property of (-)-9-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine

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Technology Process of (-)-9-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine

There total 7 articles about (-)-9-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine 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: 60.0%

: 1392126-64-5
(-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate

: 171721-10-1
(-)-9-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine

Guidance literature:: With aluminum isopropoxide; In dimethyl sulfoxide; at 90 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jo3012754

Reference yield: 40.0%

: 1392126-62-3
(-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate

: 171721-10-1
(-)-9-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine

Guidance literature:: With aluminum isopropoxide; In dimethyl sulfoxide; at 140 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jo3012754

Reference yield:

: 16838-89-4,17073-88-0,60933-68-8,60933-69-9,73068-66-3,89361-52-4,89615-42-9,89615-45-2,96192-07-3
2,3,5-tri-O-benzyl-D-lyxofuranoside

: 171721-10-1
(-)-9-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / hexane; tetrahydrofuran; benzene / 2 h / 0 - 25 °C / Inert atmosphere

1.2: 2 h / 0 - 100 °C

2.1: triethylamine; dmap / dichloromethane / 16 h / 0 - 50 °C / Inert atmosphere

3.1: ozone / dichloromethane / 0.67 h / -78 °C

3.2: 0.5 h / 25 °C

4.1: magnesium bromide diethyl etherate / dichloromethane; acetonitrile / 6 h / -40 °C / Inert atmosphere

5.1: aluminum isopropoxide / dimethyl sulfoxide / 3 h / 90 °C / Inert atmosphere

With dmap; n-butyllithium; magnesium bromide diethyl etherate; aluminum isopropoxide; ozone; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene; 1.1: |Wittig-Horner Reaction / 1.2: |Wittig-Horner Reaction;
DOI:10.1021/jo3012754