4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-pyrimidine

Base Information

• Chemical Name: 4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-pyrimidine
• CAS No.: 263006-30-0
• Molecular Formula: C₂₄H₂₆N₂O₃S
• Molecular Weight: 422.548

Synonyms:4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-pyrimidine

Chemical Property of 4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-pyrimidine

Chemical Property:

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Technology Process of 4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-pyrimidine

There total 6 articles about 4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-pyrimidine 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: 62.0%

S-methylisothiourea hydrochloride (53114-57-1) + 1-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-trimethylsilanyl-propynone (263006-26-4) → 4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-pyrimidine (263006-30-0)

Guidance literature:

With sodium carbonate; In water; acetonitrile; at 80 ℃; for 24h;

DOI:10.1016/S0040-4039(99)02078-X

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → 4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-pyrimidine (263006-30-0)

Guidance literature:

Multi-step reaction with 5 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: 62 percent / Na₂CO₃ / acetonitrile; H₂O / 24 h / 80 °C

With hydrogenchloride; 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;

DOI:10.1016/S0040-4039(99)02078-X

Reference yield:

benzyl bromide (100-39-0) → 4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-pyrimidine (263006-30-0)

Guidance literature:

Multi-step reaction with 5 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: 62 percent / Na₂CO₃ / acetonitrile; H₂O / 24 h / 80 °C

With hydrogenchloride; 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;

DOI:10.1016/S0040-4039(99)02078-X

upstream raw materials:

S-methylisothiourea hydrochloride

1-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-trimethylsilanyl-propynone

D-2-deoxyribose

benzyl bromide

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