5-((E)-3-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

Base Information

• Chemical Name: 5-((E)-3-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
• CAS No.: 1251854-63-3
• Molecular Formula: C₃₆H₄₄O₇Si
• Molecular Weight: 616.827
• Mol file: 1251854-63-3.mol

Synonyms:5-((E)-3-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

Chemical Property of 5-((E)-3-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-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-((E)-3-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

There total 15 articles about 5-((E)-3-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-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: 78.0%

7-methoxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxine-5-carbaldehyde + 5-((2-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)sulfonyl)-1-phenyl-1H-tetrazole → 5-((E)-3-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (1251854-63-3)

Guidance literature:

5-((2-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)sulfonyl)-1-phenyl-1H-tetrazole; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.666667h;

7-methoxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxine-5-carbaldehyde; In tetrahydrofuran; at -78 - 20 ℃; for 1h;

DOI:10.1039/d0ob00237b

Reference yield:

7-methoxy-2,2-dimethyl-5-vinyl-4H-benzo[d][1,3]dioxin-4-one (1005348-03-7) + C25H34O3Si (1251854-62-2) → C36H44O7Si + 5-((E)-3-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (1251854-63-3)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 80 ℃; for 36h; optical yield given as %de;

DOI:10.1016/j.tetlet.2010.07.122

Reference yield:

7-methoxy-2,2-dimethyl-5-vinyl-4H-benzo[d][1,3]dioxin-4-one (1005348-03-7) → 5-((E)-3-((4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-en-1-yl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (1251854-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine; ozone / dichloromethane / -78 - -40 °C

2.1: potassium hexamethylsilazane; 18-crown-6 ether / tetrahydrofuran / 0.67 h / -78 °C

2.2: 1 h / -78 - 20 °C

With 18-crown-6 ether; potassium hexamethylsilazane; ozone; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/d0ob00237b

upstream raw materials:

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

C₂₅H₃₄O₃Si

1,2:3,4-di-O-isopropylidene-6-iodo-D-galactopyranose

(S)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]ethane-1,2-diol