3-{3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-hydroxy-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester

Base Information

Chemical Name:3-{3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-hydroxy-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester
CAS No.:184166-93-6
Molecular Formula:C₃₉H₃₇N₇O₁₁
Molecular Weight:779.763
Hs Code.:

3-{3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-hydroxy-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester

Synonyms:3-{3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-hydroxy-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester

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Chemical Property of 3-{3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-hydroxy-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester

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Technology Process of 3-{3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-hydroxy-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester

There total 5 articles about 3-{3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-hydroxy-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl 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: 92.0%

: 184166-88-9
3-[3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-(tert-butyl-diphenyl-silanyloxy)-pent-1-ynyl]-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester

: 184166-93-6
3-{3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-hydroxy-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 21h; Ambient temperature;
DOI:10.1016/0968-0896(96)00139-3

Reference yield:

: 3958-60-9
2-nitrophenylmethyl bromide

: 184166-93-6
3-{3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-hydroxy-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) sodium methoxide / 1.) MeOH, RT, 1 h, 2.) DMF, RT, 2 h

2: 49 percent / AgO₂CCF₃, I₂ / CH₂Cl₂ / 18 h / Ambient temperature

3: 44 percent / PdCl₂(PPh₃)2, CuI, Et₃N / CH₂Cl₂ / 52 h / Ambient temperature

4: 92 percent / HOAc, TBAF / tetrahydrofuran / 21 h / Ambient temperature

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; iodine; sodium methylate; silver trifluoroacetate; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0968-0896(96)00139-3

Reference yield:

: 184166-82-3
4-(2-Nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester

: 184166-93-6
3-{3-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-5-hydroxy-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid 2-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 49 percent / AgO₂CCF₃, I₂ / CH₂Cl₂ / 18 h / Ambient temperature

2: 44 percent / PdCl₂(PPh₃)2, CuI, Et₃N / CH₂Cl₂ / 52 h / Ambient temperature

3: 92 percent / HOAc, TBAF / tetrahydrofuran / 21 h / Ambient temperature

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; iodine; silver trifluoroacetate; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0968-0896(96)00139-3