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-iodo-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl 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-iodo-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester
• CAS No.: 184166-98-1
• Molecular Formula: C₃₃H₃₃IN₆O₈
• Molecular Weight: 768.565

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-iodo-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

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-iodo-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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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-iodo-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

There total 6 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-iodo-pent-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: 84.0%

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 methyl ester (184166-94-7) → 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-iodo-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester (184166-98-1)

Guidance literature:

With methyltriphenoxyphosphonium iodide; In dichloromethane; 1.) -78 deg C, 0.5 h, 2.) RT, 2.5 h;

DOI:10.1016/0968-0896(96)00139-3

Reference yield:

methyl 4-hydroxylbenzoate (99-76-3,156291-94-0) → 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-iodo-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester (184166-98-1)

Guidance literature:

Multi-step reaction with 5 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

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; iodine; sodium methylate; silver trifluoroacetate; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0968-0896(96)00139-3

Reference yield:

2-nitrophenylmethyl bromide (3958-60-9) → 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-iodo-pent-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester (184166-98-1)

Guidance literature:

Multi-step reaction with 5 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

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; iodine; sodium methylate; silver trifluoroacetate; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0968-0896(96)00139-3

upstream raw materials:

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 methyl ester

methyl 4-hydroxylbenzoate

2-nitrophenylmethyl bromide

4-(2-Nitro-benzyloxy)-benzoic acid methyl ester

Downstream raw materials:

3-{6-Amino-3-[(3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-6-methoxycarbonyl-hex-1-ynyl}-4-(2-nitro-benzyloxy)-benzoic acid methyl ester

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

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

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