Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl ester
• CAS No.: 385827-48-5
• Molecular Formula: C₂₄H₂₈N₂O₉
• Molecular Weight: 488.494
• Mol file: 385827-48-5.mol

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl ester

There total 3 articles about Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl 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: 54.0%

Acetic acid (3R,4S,5R,6R)-2,3-diacetoxy-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl ester + O,O'-bis-(trimethylsilyl)uracil (10457-14-4) → Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl ester (385827-48-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane;

DOI:10.1021/ol010212g

Reference yield:

(3R,4S,5S,6R)-3,4-Dihydroxy-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]nonan-2-one → Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl ester (385827-48-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DIBAl-H / CH₂Cl₂; hexane / 3 h / -78 °C

1.2: pyridine / CH₂Cl₂; hexane / 10 h / 20 °C

2.1: 54 percent / TMSOTf / 1,2-dichloro-ethane

With trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; In hexane; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ol010212g

Reference yield:

(5S,6R)-6-(4-Methoxy-benzyloxy)-1-oxa-spiro[4.4]non-3-en-2-one (341032-34-6) → Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl ester (385827-48-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 42 percent / potassium permanganate; dicyclohexyl-18-crown-6 / CH₂Cl₂ / 4 h / -10 °C

2.1: DIBAl-H / CH₂Cl₂; hexane / 3 h / -78 °C

2.2: pyridine / CH₂Cl₂; hexane / 10 h / 20 °C

3.1: 54 percent / TMSOTf / 1,2-dichloro-ethane

With perhydrodibenzo-18-crown-6; potassium permanganate; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; In hexane; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ol010212g

upstream raw materials:

O,O'-bis-(trimethylsilyl)uracil

(5S,6R)-6-(4-Methoxy-benzyloxy)-1-oxa-spiro[4.4]non-3-en-2-one