Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester

Base Information

• Chemical Name: Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester
• CAS No.: 188404-22-0
• Molecular Formula: C₂₀H₂₂N₂O₉
• Molecular Weight: 434.403
• Mol file: 188404-22-0.mol

Synonyms:Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester

Chemical Property of Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester

There total 2 articles about Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-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:

2'-O-allyl-5-methyl uridine → Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester (188404-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / OsO₄, NaIO₄ / dioxane; H₂O / Ambient temperature

2: 1.) pyridine, 2.) 75percent aq. HCOOH / 1.) CH₂Cl₂, room temp., 2.) 50 deg C

With pyridine; sodium periodate; osmium(VIII) oxide; formic acid; In 1,4-dioxane; water;

DOI:10.1016/S0960-894X(96)00607-5

Reference yield:

Phenoxyacetyl chloride (701-99-5) + 1-((4aR,5R,7R,7aR)-2-Hydroxy-7-hydroxymethyl-hexahydro-furo[3,4-b][1,4]dioxin-5-yl)-5-methyl-1H-pyrimidine-2,4-dione (188404-21-9) → Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester (188404-22-0)

Guidance literature:

With pyridine; formic acid; Yield given. Multistep reaction; 1.) CH₂Cl₂, room temp., 2.) 50 deg C;

DOI:10.1016/S0960-894X(96)00607-5

Reference yield: 70.0%

Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-hydroxy-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester (188404-22-0) + Diphenylphosphinic chloride (1499-21-4) → Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-(diphenyl-phosphinoyloxy)-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester (188404-23-1)

Guidance literature:

With pyridine; dmap; In acetonitrile; at 0 ℃;

DOI:10.1016/S0960-894X(96)00607-5

upstream raw materials:

Phenoxyacetyl chloride

1-((4aR,5R,7R,7aR)-2-Hydroxy-7-hydroxymethyl-hexahydro-furo[3,4-b][1,4]dioxin-5-yl)-5-methyl-1H-pyrimidine-2,4-dione

Downstream raw materials:

Phenoxy-acetic acid (4aR,5R,7R,7aR)-3-(diphenyl-phosphinoyloxy)-7-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,4-b][1,4]dioxin-5-ylmethyl ester

C₃₈H₄₆N₄O₁₁Si