9-benzyl-2-[N³-allyl-5-methyl-2,4(1H,3H)-pyrimidinedion-1-yl]-perhydro-6,8-(epoxyimino)furo[3,2-b]oxepin

Base Information

• Chemical Name: 9-benzyl-2-[N³-allyl-5-methyl-2,4(1H,3H)-pyrimidinedion-1-yl]-perhydro-6,8-(epoxyimino)furo[3,2-b]oxepin
• CAS No.: 189265-38-1
• Molecular Formula: C₂₃H₂₇N₃O₅
• Molecular Weight: 425.484

Synonyms:9-benzyl-2-[N³-allyl-5-methyl-2,4(1H,3H)-pyrimidinedion-1-yl]-perhydro-6,8-(epoxyimino)furo[3,2-b]oxepin

Chemical Property of 9-benzyl-2-[N³-allyl-5-methyl-2,4(1H,3H)-pyrimidinedion-1-yl]-perhydro-6,8-(epoxyimino)furo[3,2-b]oxepin

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Technology Process of 9-benzyl-2-[N³-allyl-5-methyl-2,4(1H,3H)-pyrimidinedion-1-yl]-perhydro-6,8-(epoxyimino)furo[3,2-b]oxepin

There total 4 articles about 9-benzyl-2-[N³-allyl-5-methyl-2,4(1H,3H)-pyrimidinedion-1-yl]-perhydro-6,8-(epoxyimino)furo[3,2-b]oxepin 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: 86.0%

N-benzyl hydroxylalmine (622-30-0) + 3-allyloxy-2-formyl-5-(N3-allyl thymin-1-yl)-tetrahydrofuran (189265-37-0) → 9-benzyl-2-[N3-allyl-5-methyl-2,4(1H,3H)-pyrimidinedion-1-yl]-perhydro-6,8-(epoxyimino)furo[3,2-b]oxepin (189265-38-1)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; at 20 ℃; for 14h; Heating;

DOI:10.1016/S0040-4020(97)00141-5

Reference yield:

5'-O-tritylthymidine (7791-71-1) → 9-benzyl-2-[N3-allyl-5-methyl-2,4(1H,3H)-pyrimidinedion-1-yl]-perhydro-6,8-(epoxyimino)furo[3,2-b]oxepin (189265-38-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / dimethylformamide / 1 h / 0 - 5 °C

1.2: 75 percent / dimethylformamide / 20 h

2.1: 72 percent / acetic acid; water / 5 h / 80 °C

3.1: pyridine; trifluoroacetic acid; DCC / dimethylsulfoxide; benzene / 18 h / 20 °C

3.2: 76 percent / oxalic acid / dimethylsulfoxide; benzene; methanol / 0.5 h

4.1: 86 percent / NaHCO₃ / ethanol / 14 h / 20 °C / Heating

With pyridine; water; sodium hydride; sodium hydrogencarbonate; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 1.1: Metallation / 1.2: allylation / 2.1: detritylation / 3.1: Moffatt oxidation / 3.2: Moffatt oxidation / 4.1: Cyclization;

DOI:10.1016/S0040-4020(97)00141-5

Reference yield:

3'-O-,N3-diallyl thymidine (189265-36-9) → 9-benzyl-2-[N3-allyl-5-methyl-2,4(1H,3H)-pyrimidinedion-1-yl]-perhydro-6,8-(epoxyimino)furo[3,2-b]oxepin (189265-38-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine; trifluoroacetic acid; DCC / dimethylsulfoxide; benzene / 18 h / 20 °C

1.2: 76 percent / oxalic acid / dimethylsulfoxide; benzene; methanol / 0.5 h

2.1: 86 percent / NaHCO₃ / ethanol / 14 h / 20 °C / Heating

With pyridine; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; In ethanol; dimethyl sulfoxide; benzene; 1.1: Moffatt oxidation / 1.2: Moffatt oxidation / 2.1: Cyclization;

DOI:10.1016/S0040-4020(97)00141-5

upstream raw materials:

N-benzyl hydroxylalmine

3-allyloxy-2-formyl-5-(N³-allyl thymin-1-yl)-tetrahydrofuran

5'-O-tritylthymidine

3'-O-,N³-diallyl thymidine

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