3-{6-Amino-3-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-6-methoxycarbonyl-hex-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

Base Information

Chemical Name:3-{6-Amino-3-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-6-methoxycarbonyl-hex-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester
CAS No.:184167-07-5
Molecular Formula:C₃₃H₃₅N₇O₁₀
Molecular Weight:689.682
Hs Code.:

3-{6-Amino-3-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-6-methoxycarbonyl-hex-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

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Chemical Property of 3-{6-Amino-3-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-6-methoxycarbonyl-hex-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

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Technology Process of 3-{6-Amino-3-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-6-methoxycarbonyl-hex-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

There total 9 articles about 3-{6-Amino-3-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-6-methoxycarbonyl-hex-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl 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:

: 99-76-3,156291-94-0
methyl 4-hydroxylbenzoate

: 184167-07-5
3-{6-Amino-3-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-6-methoxycarbonyl-hex-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) sodium methoxide / 1.) MeOH, RT, 20 min, 2.) DMF, RT, 30 min

2: 92 percent / silver trifluoroacetate, I₂ / CH₂Cl₂ / 19 h / Ambient temperature

3: 75 percent / PdCl₂(PPh₃)2, CuI, Et₃N / CH₂Cl₂ / 20 h

4: 99 percent / HOAc, TBAF / tetrahydrofuran / 17 h / Ambient temperature

5: 84 percent / (PhO)3P⁽¹⁺⁾*CH₃I^(1-) / CH₂Cl₂ / 1.) -78 deg C, 0.5 h, 2.) RT, 2.5 h

6: 1.) diisopropylamine, HMPA, n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to 0 deg C

7: glac. AcOH / CH₂Cl₂ / 3 h

8: 80percent aq. HCOOH / 3 h / Ambient temperature

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

Reference yield:

: 3958-60-9
2-nitrophenylmethyl bromide

: 184167-07-5
3-{6-Amino-3-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-6-methoxycarbonyl-hex-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) sodium methoxide / 1.) MeOH, RT, 20 min, 2.) DMF, RT, 30 min

2: 92 percent / silver trifluoroacetate, I₂ / CH₂Cl₂ / 19 h / Ambient temperature

3: 75 percent / PdCl₂(PPh₃)2, CuI, Et₃N / CH₂Cl₂ / 20 h

4: 99 percent / HOAc, TBAF / tetrahydrofuran / 17 h / Ambient temperature

5: 84 percent / (PhO)3P⁽¹⁺⁾*CH₃I^(1-) / CH₂Cl₂ / 1.) -78 deg C, 0.5 h, 2.) RT, 2.5 h

6: 1.) diisopropylamine, HMPA, n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to 0 deg C

7: glac. AcOH / CH₂Cl₂ / 3 h

8: 80percent aq. HCOOH / 3 h / Ambient temperature

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

Reference yield:

: 184166-83-4
4-(2-Nitro-benzyloxy)-benzoic acid methyl ester

: 184167-07-5
3-{6-Amino-3-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-6-methoxycarbonyl-hex-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / silver trifluoroacetate, I₂ / CH₂Cl₂ / 19 h / Ambient temperature

2: 75 percent / PdCl₂(PPh₃)2, CuI, Et₃N / CH₂Cl₂ / 20 h

3: 99 percent / HOAc, TBAF / tetrahydrofuran / 17 h / Ambient temperature

4: 84 percent / (PhO)3P⁽¹⁺⁾*CH₃I^(1-) / CH₂Cl₂ / 1.) -78 deg C, 0.5 h, 2.) RT, 2.5 h

5: 1.) diisopropylamine, HMPA, n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to 0 deg C

6: glac. AcOH / CH₂Cl₂ / 3 h

7: 80percent aq. HCOOH / 3 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; formic acid; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; iodine; silver trifluoroacetate; acetic acid; triethylamine; diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0968-0896(96)00139-3