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

Base Information

Chemical Name:1-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-trimethylsilanyl-propynone
CAS No.:263006-26-4
Molecular Formula:C₂₅H₃₀O₄Si
Molecular Weight:422.596
Hs Code.:

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

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

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

There total 5 articles about 1-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-trimethylsilanyl-propynone 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: 100.0%

: 54655-07-1
lithium trimethylsilylacetylenide

: 263006-25-3
(2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide

: 263006-26-4
1-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-trimethylsilanyl-propynone

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 3h;
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

: 263006-26-4
1-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-trimethylsilanyl-propynone

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 100-39-0
benzyl bromide

: 263006-26-4
1-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-trimethylsilanyl-propynone

Guidance literature:: Multi-step reaction with 4 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

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