(2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate

Base Information

Chemical Name:(2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate
CAS No.:1610605-74-7
Molecular Formula:C₃₅H₃₆ClN₅O₈S
Molecular Weight:722.219
Hs Code.:

Synonyms:(2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate

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Chemical Property of (2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate

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Technology Process of (2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate

There total 6 articles about (2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate 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:

: 10310-21-1
2-Amino-6-chloropurin

: 452949-21-2
(3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate

: 1610605-74-7
(2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate

Guidance literature:: 2-Amino-6-chloropurin; With N,O-bis-(trimethylsilyl)-acetamide; In 1,2-dichloro-ethane; for 0.5h; Reflux;

(3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-2,3-diyl diacetate; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 70 ℃; for 1.5h; Inert atmosphere;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 233266-76-7
(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

: 1610605-74-7
(2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 1.17 h / 0 - 20 °C / Inert atmosphere

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 18.5 h / 20 °C / Inert atmosphere

2.2: 2.5 h / 20 °C / Inert atmosphere

3.1: triethylamine; dmap / dichloromethane / 18 h / 20 °C

4.1: sulfuric acid / acetic acid / 1 h / 20 °C

5.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 0.5 h / Reflux

5.2: 1.5 h / 70 °C / Inert atmosphere

With dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; triethylamine; In tetrahydrofuran; dichloromethane; acetic acid; 1,2-dichloro-ethane;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 287737-63-7
(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole

: 1610605-74-7
(2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 18.5 h / 20 °C / Inert atmosphere

1.2: 2.5 h / 20 °C / Inert atmosphere

2.1: triethylamine; dmap / dichloromethane / 18 h / 20 °C

3.1: sulfuric acid / acetic acid / 1 h / 20 °C

4.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 0.5 h / Reflux

4.2: 1.5 h / 70 °C / Inert atmosphere

With dmap; 9-borabicyclo[3.3.1]nonane dimer; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; triethylamine; In tetrahydrofuran; dichloromethane; acetic acid; 1,2-dichloro-ethane;
DOI:10.1016/j.bmcl.2014.04.050