6-(6-methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl-acetaldehyde

Base Information

• Chemical Name: 6-(6-methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl-acetaldehyde
• CAS No.: 549513-49-7
• Molecular Formula: C₂₄H₂₈O₅
• Molecular Weight: 396.483
• Mol file: 549513-49-7.mol

Synonyms:6-(6-methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl-acetaldehyde

Chemical Property of 6-(6-methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(6-methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl-acetaldehyde

There total 11 articles about 6-(6-methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl-acetaldehyde 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: 90.0%

ethyl (2S,4S,6S)-6-[[(2S,4S,6S)-6-methyl-2-phenyl-1,3-dioxan-4-yl]methyl]-2-phenyl-1,3-dioxane-4-acetate (549513-47-5) → 6-(6-methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl-acetaldehyde (549513-49-7)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.666667h;

DOI:10.1021/ol0345529

Reference yield:

((2S,4S,6S)-6-Methyl-2-phenyl-[1,3]dioxan-4-yl)-acetaldehyde (188924-70-1) → 6-(6-methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl-acetaldehyde (549513-49-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 230 mg / LiCl; i-Pr₂NEt / acetonitrile / 20 °C

2.1: 90 percent / Sm(OiPr)3; 4 Angstroem molecular sieves; AsPh₃O / (S)-BINOL; tert-butyl hydroperoxide / tetrahydrofuran; decane / 8 h / 20 °C

3.1: LHMDS / tetrahydrofuran / 0.42 h / -78 °C

3.2: 88 percent / tetrahydrofuran / 4 h / -78 °C

4.1: 77 percent / NaBH₄; PhSeSePh / ethanol / 0.08 h / 20 °C

5.1: Et₂B(OMe) / tetrahydrofuran; methanol / 1 h / -78 °C

5.2: NaBH₄ / tetrahydrofuran; methanol / 8 h / -78 - -40 °C

6.1: 246 mg / TsOH*H₂O / toluene / 20 °C

7.1: B(OMe)3; LiBH₄ / diethyl ether / 0.33 h / 20 °C

8.1: 46 mg / N-methylmorpholine-N-oxide; 4 Angstroem molecular sieves; TPAP / CH₂Cl₂ / 0.5 h / 20 °C

With sodium tetrahydroborate; lithium borohydride; tetrapropylammonium perruthennate; Trimethyl borate; 4 A molecular sieve; diphenyl diselenide; diethyl methoxy borane; triphenylarsineoxide; samarium(III) isopropoxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium hexamethyldisilazane; tert.-butylhydroperoxide; (S)-[1,1']-binaphthalenyl-2,2'-diol; In tetrahydrofuran; methanol; diethyl ether; decane; ethanol; dichloromethane; toluene; acetonitrile;

DOI:10.1002/chem.200305709

Reference yield:

2-[(2R,4R,6R)-6-((2S,4S,6S)-6-Methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl]-ethanol → 6-(6-methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl-acetaldehyde (549513-49-7)

Guidance literature:

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/chem.200305709

upstream raw materials:

ethyl (2S,4S,6S)-6-[[(2S,4S,6S)-6-methyl-2-phenyl-1,3-dioxan-4-yl]methyl]-2-phenyl-1,3-dioxane-4-acetate

((2S,4S,6S)-6-Methyl-2-phenyl-[1,3]dioxan-4-yl)-acetaldehyde

2-((2S,4R,6S)-6-Methyl-2-phenyl-[1,3]dioxan-4-yl)-ethanol

4-[(E)-4-[(2S,4R,6S)-6-methyl-2-phenyl-1,3-dioxan-4-yl]-1-oxo-2-butenyl]morpholine

Downstream raw materials:

ethyl (Z)-4-[(2R,4R,6R)-6-[[(2S,4S,6S)-6-methyl-2-phenyl-1,3-dioxan-4-yl]methyl]-2-phenyl-1,3-dioxan-4-yl]-2-butenoate

4-[6-(6-methyl-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-phenyl-[1,3]dioxan-4-yl]-but-2Z-enoic acid methyl ester