1,3-Dioxane-4-methanol, 5-azido-2,2-dimethyl-6-phenyl-, (4R,5S,6R)-

Base Information

• Chemical Name: 1,3-Dioxane-4-methanol, 5-azido-2,2-dimethyl-6-phenyl-, (4R,5S,6R)-
• CAS No.: 591721-43-6
• Molecular Formula: C13H17N3O3
• Molecular Weight: 263.296
• Mol file: 591721-43-6.mol

Synonyms:

Chemical Property of 1,3-Dioxane-4-methanol, 5-azido-2,2-dimethyl-6-phenyl-, (4R,5S,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3-Dioxane-4-methanol, 5-azido-2,2-dimethyl-6-phenyl-, (4R,5S,6R)-

There total 5 articles about 1,3-Dioxane-4-methanol, 5-azido-2,2-dimethyl-6-phenyl-, (4R,5S,6R)- 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: 85.0%

5-azido-2,2-dimethyl-(SS)-4-(4-methylphenylsulfinylmethyl)-6-phenyl-(4S,5R,6R)-1,3-dioxane (591721-41-4) → 5-azido-2,2-dimethyl-6-phenyl-(4R,5S,6R)-1,3-dioxan-4-ylmethanol (591721-43-6)

Guidance literature:

5-azido-2,2-dimethyl-(S_S)-4-(4-methylphenylsulfinylmethyl)-6-phenyl-(4S,5R,6R)-1,3-dioxane; With triethylamine; trifluoroacetic anhydride; In acetonitrile; at 0 ℃; for 0.166667h;

With sodium tetrahydroborate; sodium hydrogencarbonate; In acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1016/S0957-4166(03)00239-8

Reference yield:

(R,E)-4-phenyl-1-(p-tolylsulfinyl)but-3-en-2-one (95482-76-1) → 5-azido-2,2-dimethyl-6-phenyl-(4R,5S,6R)-1,3-dioxan-4-ylmethanol (591721-43-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / DIBAL-H; ZnCl₂ / tetrahydrofuran; toluene / 1 h / -78 °C

2.1: 80 percent / NBS; H₂O / toluene / 0.5 h / 20 °C

3.1: 90 percent / CSA / acetone / 1 h / 20 °C

4.1: 75 percent / NaN₃ / dimethylsulfoxide / 8 h / 100 °C

5.1: trifluoroacetic anhydride; Et₃N / acetonitrile / 0.17 h / 0 °C

5.2: 85 percent / aq. NaHCO₃; NaBH₄ / acetonitrile / 0.5 h / 0 °C

With N-Bromosuccinimide; sodium azide; camphor-10-sulfonic acid; water; diisobutylaluminium hydride; triethylamine; trifluoroacetic anhydride; zinc(II) chloride; In tetrahydrofuran; dimethyl sulfoxide; acetone; toluene; acetonitrile;

DOI:10.1016/S0957-4166(03)00239-8

Reference yield:

1-(4-methylphenylsulfinyl)-4-phenyl-(2R,3E)-3-buten-2-ol (95482-80-7) → 5-azido-2,2-dimethyl-6-phenyl-(4R,5S,6R)-1,3-dioxan-4-ylmethanol (591721-43-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / NBS; H₂O / toluene / 0.5 h / 20 °C

2.1: 90 percent / CSA / acetone / 1 h / 20 °C

3.1: 75 percent / NaN₃ / dimethylsulfoxide / 8 h / 100 °C

4.1: trifluoroacetic anhydride; Et₃N / acetonitrile / 0.17 h / 0 °C

4.2: 85 percent / aq. NaHCO₃; NaBH₄ / acetonitrile / 0.5 h / 0 °C

With N-Bromosuccinimide; sodium azide; camphor-10-sulfonic acid; water; triethylamine; trifluoroacetic anhydride; In dimethyl sulfoxide; acetone; toluene; acetonitrile;

DOI:10.1016/S0957-4166(03)00239-8

upstream raw materials:

5-azido-2,2-dimethyl-(S_S)-4-(4-methylphenylsulfinylmethyl)-6-phenyl-(4S,5R,6R)-1,3-dioxane

(R,E)-4-phenyl-1-(p-tolylsulfinyl)but-3-en-2-one

1-(4-methylphenylsulfinyl)-4-phenyl-(2R,3E)-3-buten-2-ol

2-bromo-(S_S)-4-(4-methylphenylsulfinyl)-1-phenyl-(2R,2R,3S)-butane-1,3-diol

Downstream raw materials:

(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

methyl 3-azido-2,4-dihydroxy-4-phenyl-(2R,3S,4R)-butanoate

methyl 5-azido-2,2-dimethyl-6-phenyl-(4R,5S,6R)-1,3-dioxane-4-carboxylate