(2R,3S)-2-Hydroxymethyl-5-(2-methyl-6-phenyl-pyrimidin-4-yl)-tetrahydro-furan-3-ol

Base Information

Chemical Name:(2R,3S)-2-Hydroxymethyl-5-(2-methyl-6-phenyl-pyrimidin-4-yl)-tetrahydro-furan-3-ol
CAS No.:263006-38-8
Molecular Formula:C₁₆H₁₈N₂O₃
Molecular Weight:286.331
Hs Code.:

Synonyms:(2R,3S)-2-Hydroxymethyl-5-(2-methyl-6-phenyl-pyrimidin-4-yl)-tetrahydro-furan-3-ol

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Chemical Property of (2R,3S)-2-Hydroxymethyl-5-(2-methyl-6-phenyl-pyrimidin-4-yl)-tetrahydro-furan-3-ol

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Technology Process of (2R,3S)-2-Hydroxymethyl-5-(2-methyl-6-phenyl-pyrimidin-4-yl)-tetrahydro-furan-3-ol

There total 6 articles about (2R,3S)-2-Hydroxymethyl-5-(2-methyl-6-phenyl-pyrimidin-4-yl)-tetrahydro-furan-3-ol 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: 76.0%

: 263006-33-3
4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methyl-6-phenyl-pyrimidine

: 263006-38-8
(2R,3S)-2-Hydroxymethyl-5-(2-methyl-6-phenyl-pyrimidin-4-yl)-tetrahydro-furan-3-ol

Guidance literature:: With boron trichloride; In dichloromethane; at 20 ℃;
DOI:10.1016/S0040-4039(99)02078-X

Reference yield:

: 452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3
D-2-deoxyribose

: 263006-38-8
(2R,3S)-2-Hydroxymethyl-5-(2-methyl-6-phenyl-pyrimidin-4-yl)-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: AcCl; Ag₂CO₃ / methanol / 0.12 h / 20 °C

1.2: NaH; Bu₄NI / dimethylformamide / 24 h / -30 - 20 °C

1.3: TMSOTf / CH₂Cl₂ / 24 h / 20 °C

2.1: 100 percent / HCl / dioxane / 4 h / 100 °C

3.1: α,α-dichloromethylmethyl ether / CH2Cl2 / 5 h / Heating

3.2: 85 percent / NEt₃ / CH₂Cl₂ / 24 h / 20 °C

4.1: 100 percent / tetrahydrofuran / 3 h / -78 °C

5.1: 85 percent / Na₂CO₃ / acetonitrile; H₂O / 24 h / 80 °C

6.1: 76 percent / BCl₃ / CH₂Cl₂ / 20 °C

With hydrogenchloride; boron trichloride; sodium carbonate; acetyl chloride; silver carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile; 1.1: Acetylation / 1.2: Etherification / 1.3: Substitution / 2.1: Hydrolysis / 3.1: activation / 3.2: Substitution / 4.1: Substitution / 5.1: Condensation / 6.1: dealkylation;
DOI:10.1016/S0040-4039(99)02078-X

Reference yield:

: 226232-74-2
1α-cyano-3,5-di-O-benzyl-1,2-dideoxy-D-ribofuranose

: 263006-38-8
(2R,3S)-2-Hydroxymethyl-5-(2-methyl-6-phenyl-pyrimidin-4-yl)-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / HCl / dioxane / 4 h / 100 °C

2.1: α,α-dichloromethylmethyl ether / CH2Cl2 / 5 h / Heating

2.2: 85 percent / NEt₃ / CH₂Cl₂ / 24 h / 20 °C

3.1: 100 percent / tetrahydrofuran / 3 h / -78 °C

4.1: 85 percent / Na₂CO₃ / acetonitrile; H₂O / 24 h / 80 °C

5.1: 76 percent / BCl₃ / CH₂Cl₂ / 20 °C

With hydrogenchloride; boron trichloride; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile; 1.1: Hydrolysis / 2.1: activation / 2.2: Substitution / 3.1: Substitution / 4.1: Condensation / 5.1: dealkylation;
DOI:10.1016/S0040-4039(99)02078-X