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

Base Information

• Chemical Name: (5S,6R)-6-(4-Methoxy-benzyloxy)-1-oxa-spiro[4.4]non-3-en-2-one
• CAS No.: 341032-34-6
• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.317
• Mol file: 341032-34-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (5S,6R)-6-(4-Methoxy-benzyloxy)-1-oxa-spiro[4.4]non-3-en-2-one 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: 71.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + (5S,6R)-6-Hydroxy-1-oxa-spiro[4.4]non-3-en-2-one (496050-93-2) → (5S,6R)-6-(4-Methoxy-benzyloxy)-1-oxa-spiro[4.4]non-3-en-2-one (341032-34-6)

Guidance literature:

With trifluorormethanesulfonic acid;

DOI:10.1021/jo010026o

Reference yield: 65.0%

(5S,6R)-6-(4-Methoxy-benzyloxy)-1-oxa-spiro[4.4]non-3-ene (341032-28-8) → (5S,6R)-6-(4-Methoxy-benzyloxy)-1-oxa-spiro[4.4]non-3-en-2-one (341032-34-6) + 4-Methoxy-benzoic acid (5S,6R)-2-oxo-1-oxa-spiro[4.4]non-3-en-6-yl ester

Guidance literature:

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; pyridinium chlorochromate; In dichloromethane; at -20 ℃; for 1h;

DOI:10.1021/jo010026o

Reference yield:

C16H22BrNO3S → (5S,6R)-6-(4-Methoxy-benzyloxy)-1-oxa-spiro[4.4]non-3-en-2-one (341032-34-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 77 percent / xylene / 10 h / Heating

2.1: 89 percent / sodium borohydride; cerium trichloride heptahydrate / methanol

3.1: sodium hydride / dimethylformamide / 1.5 h

3.2: 91 percent / dimethylformamide / 20 °C

4.1: 65 percent / PCC; CrO₃; 3,5-dimethylpyrazole / CH₂Cl₂ / 1 h / -20 °C

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; sodium tetrahydroborate; cerium(III) chloride; sodium hydride; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide; xylene;

DOI:10.1021/jo010026o

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

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

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

(+)-4-bromo-1-oxaspiro[4.4]nonan-6-one

Downstream raw materials:

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