5-((2S,4S)-2-(benzyloxy)-4-hydroxyhept-6-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

Base Information

• Chemical Name: 5-((2S,4S)-2-(benzyloxy)-4-hydroxyhept-6-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
• CAS No.: 1394226-64-2
• Molecular Formula: C₂₅H₃₀O₆
• Molecular Weight: 426.51
• Mol file: 1394226-64-2.mol

Synonyms:

Chemical Property of 5-((2S,4S)-2-(benzyloxy)-4-hydroxyhept-6-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-((2S,4S)-2-(benzyloxy)-4-hydroxyhept-6-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

There total 8 articles about 5-((2S,4S)-2-(benzyloxy)-4-hydroxyhept-6-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-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:

(S)-3-(benzyloxy)-4-(7-methoxy-2,2-dimethyl-4-oxo-4Hbenzo[d][1,3]dioxin-5-yl)butanal (1394226-63-1) + allyltributylstanane (24850-33-7) → 5-((2S,4R)-2-(benzyloxy)-4-hydroxyhept-6-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one + 5-((2S,4S)-2-(benzyloxy)-4-hydroxyhept-6-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (1394226-64-2)

Guidance literature:

(S)-3-(benzyloxy)-4-(7-methoxy-2,2-dimethyl-4-oxo-4Hbenzo[d][1,3]dioxin-5-yl)butanal; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.166667h;

allyltributylstanane; In dichloromethane; for 3h; Overall yield = 80%; Overall yield = 39.9 mg; Optical yield = 63.636 %de; diastereoselective reaction;

DOI:10.1021/jo301167a

Reference yield:

5-hydroxy-7-methoxy-2,2-dimethyl-benzo[1,3]dioxin-4-one (532394-23-3) → 5-((2S,4S)-2-(benzyloxy)-4-hydroxyhept-6-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (1394226-64-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / 24 h / 0 °C

2.1: cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h

2.2: 24 h / Reflux

3.1: ozone / dichloromethane; methanol / -78 °C

4.1: diethyl ether / 1 h / -78 °C / Inert atmosphere

5.1: magnesium oxide / benzene / 24 h / 83 °C

6.1: ozone / dichloromethane; methanol / -78 °C

7.1: titanium tetrachloride / dichloromethane / 0.17 h / -78 °C

7.2: 3 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; magnesium oxide; titanium tetrachloride; ozone; cesium fluoride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene; 2.1: |Suzuki Coupling / 2.2: |Suzuki Coupling / 7.1: |Keck Asymmetric Allylation;

DOI:10.1021/jo301167a

Reference yield:

5,7-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (137571-73-4) → 5-((2S,4S)-2-(benzyloxy)-4-hydroxyhept-6-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (1394226-64-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triphenylphosphine / tetrahydrofuran / 0.08 h / 0 °C

1.2: 4 h / 0 °C

2.1: pyridine / 24 h / 0 °C

3.1: cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h

3.2: 24 h / Reflux

4.1: ozone / dichloromethane; methanol / -78 °C

5.1: diethyl ether / 1 h / -78 °C / Inert atmosphere

6.1: magnesium oxide / benzene / 24 h / 83 °C

7.1: ozone / dichloromethane; methanol / -78 °C

8.1: titanium tetrachloride / dichloromethane / 0.17 h / -78 °C

8.2: 3 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; magnesium oxide; titanium tetrachloride; ozone; triphenylphosphine; cesium fluoride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene; 3.1: |Suzuki Coupling / 3.2: |Suzuki Coupling / 8.1: |Keck Asymmetric Allylation;

DOI:10.1021/jo301167a

upstream raw materials:

5,7-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

5-hydroxy-7-methoxy-2,2-dimethyl-benzo[1,3]dioxin-4-one

2-benzyloxy-1-methylpyridinium triflate

(S)-3-(benzyloxy)-4-(7-methoxy-2,2-dimethyl-4-oxo-4Hbenzo[d][1,3]dioxin-5-yl)butanal