N-[2,4-bis(benzyloxy)-6-{[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy}pyrimidin-5-yl]isobutyramide

Base Information

Chemical Name:N-[2,4-bis(benzyloxy)-6-{[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy}pyrimidin-5-yl]isobutyramide
CAS No.:1389328-87-3
Molecular Formula:C₂₇H₃₃N₃O₈
Molecular Weight:527.574
Hs Code.:

Synonyms:N-[2,4-bis(benzyloxy)-6-{[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy}pyrimidin-5-yl]isobutyramide

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Chemical Property of N-[2,4-bis(benzyloxy)-6-{[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy}pyrimidin-5-yl]isobutyramide

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Technology Process of N-[2,4-bis(benzyloxy)-6-{[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy}pyrimidin-5-yl]isobutyramide

There total 4 articles about N-[2,4-bis(benzyloxy)-6-{[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy}pyrimidin-5-yl]isobutyramide 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: 81.0%

: N-(2,4-bis(benzyloxy)-6-(((4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methoxy)pyrimidin-5-yl)isobutyramide

: 1389328-87-3
N-[2,4-bis(benzyloxy)-6-{[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy}pyrimidin-5-yl]isobutyramide

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; at 23 ℃; for 12h;
DOI:10.1021/jo3010364

Reference yield:

: 3969-86-6,19139-74-3,30737-85-0,84709-27-3,84709-35-3,84709-41-1,127305-49-1,100484-23-9
((4S,4’R,5S)-2,2,2’,2’-tetramethyl-[4,4’-bi(1,3-dioxolan)]-5-yl)methanol

: 1389328-87-3
N-[2,4-bis(benzyloxy)-6-{[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy}pyrimidin-5-yl]isobutyramide

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -40 - 23 °C

1.2: 5 h / -40 - 20 °C

2.1: sodium dithionite / 1,4-dioxane; methanol / 9 h / 23 - 100 °C / pH 9.5 / aq. buffer

3.1: triethylamine / tetrahydrofuran / 6 h / 0 °C

4.1: hydrogenchloride / tetrahydrofuran / 12 h / 23 °C

With hydrogenchloride; sodium dithionite; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol;
DOI:10.1021/jo3010364

Reference yield:

: 2,4-bis(benzyloxy)-6-(((4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methoxy)pyrimidin-5-amine

: 1389328-87-3
N-[2,4-bis(benzyloxy)-6-{[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy}pyrimidin-5-yl]isobutyramide

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 6 h / 0 °C

2: hydrogenchloride / tetrahydrofuran / 12 h / 23 °C

With hydrogenchloride; triethylamine; In tetrahydrofuran;
DOI:10.1021/jo3010364