ethyl 2-(2,4-bis(benzyloxy)-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)pyrimidin-5-ylamino)-2-oxoacetate

Base Information

• Chemical Name: ethyl 2-(2,4-bis(benzyloxy)-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)pyrimidin-5-ylamino)-2-oxoacetate
• CAS No.: 1389328-82-8
• Molecular Formula: C₂₇H₃₁N₃O₁₀
• Molecular Weight: 557.557
• Mol file: 1389328-82-8.mol

Synonyms:ethyl 2-(2,4-bis(benzyloxy)-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)pyrimidin-5-ylamino)-2-oxoacetate

Chemical Property of ethyl 2-(2,4-bis(benzyloxy)-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)pyrimidin-5-ylamino)-2-oxoacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-(2,4-bis(benzyloxy)-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)pyrimidin-5-ylamino)-2-oxoacetate

There total 3 articles about ethyl 2-(2,4-bis(benzyloxy)-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)pyrimidin-5-ylamino)-2-oxoacetate 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: 53.0%

ethyl 2-(2,4-bis(benzyloxy)-6-(((4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methoxy)pyrimidin-5-ylamino)-2-oxoacetate → methyl 2-(2,4-bis(benzyloxy)-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)pyrimidin-5-ylamino)-2-oxoacetate (1389328-83-9) + ethyl 2-(2,4-bis(benzyloxy)-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)pyrimidin-5-ylamino)-2-oxoacetate (1389328-82-8)

Guidance literature:

With hydrogenchloride; In methanol; at 23 ℃; for 12h;

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 → ethyl 2-(2,4-bis(benzyloxy)-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)pyrimidin-5-ylamino)-2-oxoacetate (1389328-82-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 2.5 h / 0 - 23 °C

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

With hydrogenchloride; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1021/jo3010364

Reference yield:

((4S,4’R,5S)-2,2,2’,2’-tetramethyl-[4,4’-bi(1,3-dioxolan)]-5-yl)methanol (3969-86-6,19139-74-3,30737-85-0,84709-27-3,84709-35-3,84709-41-1,127305-49-1,100484-23-9) → ethyl 2-(2,4-bis(benzyloxy)-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)pyrimidin-5-ylamino)-2-oxoacetate (1389328-82-8)

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 / 2.5 h / 0 - 23 °C

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

With hydrogenchloride; sodium dithionite; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1021/jo3010364

upstream raw materials:

((4S,4’R,5S)-2,2,2’,2’-tetramethyl-[4,4’-bi(1,3-dioxolan)]-5-yl)methanol