Hexanedioic acid mono-[(3aR,4R,6R,6aR)-6-(6-benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester

Base Information

• Chemical Name: Hexanedioic acid mono-[(3aR,4R,6R,6aR)-6-(6-benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester
• CAS No.: 192052-70-3
• Molecular Formula: C₂₇H₃₁N₅O₉
• Molecular Weight: 569.571

Synonyms:

Chemical Property of Hexanedioic acid mono-[(3aR,4R,6R,6aR)-6-(6-benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Hexanedioic acid mono-[(3aR,4R,6R,6aR)-6-(6-benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester

There total 4 articles about Hexanedioic acid mono-[(3aR,4R,6R,6aR)-6-(6-benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] 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: 64.0%

adipic anhydride (2035-75-8) + N6-benzoyl-2',3'-isopropylidene adenosine (192052-69-0) → Hexanedioic acid mono-[(3aR,4R,6R,6aR)-6-(6-benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester (192052-70-3)

Guidance literature:

With dmap; In dichloromethane; for 21h;

DOI:10.1002/hlca.19970800304

Reference yield:

2',3'-isopropylidene adenosine (362-75-4) → Hexanedioic acid mono-[(3aR,4R,6R,6aR)-6-(6-benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester (192052-70-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 40 percent / pyridine / 5 h

2: 53 percent / 1.) t-BuLi / 1.) -78 deg C, 10 min; 2.) -78 deg C, 5 min, then room temp., 15 min

3: 90 percent / 1H-pyrrole, 5percent CHCl₂COOH / CH₂Cl₂ / 0.03 h / Ambient temperature

4: 64 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 21 h

With pyridine; dichloro-acetic acid; dmap; pyrrole; tert.-butyl lithium; In dichloromethane;

DOI:10.1002/hlca.19970800304

Reference yield:

(9-{(3aR,4R,6R,6aR)-6-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-yl)-carbamic acid benzyl ester (192052-71-4) → Hexanedioic acid mono-[(3aR,4R,6R,6aR)-6-(6-benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester (192052-70-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 1H-pyrrole, 5percent CHCl₂COOH / CH₂Cl₂ / 0.03 h / Ambient temperature

2: 64 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 21 h

With dichloro-acetic acid; dmap; pyrrole; In dichloromethane;

DOI:10.1002/hlca.19970800304

upstream raw materials:

adipic anhydride

N⁶-benzoyl-2',3'-isopropylidene adenosine

2',3'-isopropylidene adenosine

(9-{(3aR,4R,6R,6aR)-6-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-yl)-carbamic acid benzyl ester

Downstream raw materials:

Boc-Glu(O^tBu)-Tyr[CO(CH₂)4CO-bzoc⁶A(=CMe₂)]-Leu-morpholine

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