4-[1-tert-butyldimethylsilyloxy-3-triphenylmethyloxy-(1S)-propyl]-5-(1-ethynyl-2,2-dimethyl)-(4R,5R)-1,3-dioxolane

Base Information

Chemical Name:4-[1-tert-butyldimethylsilyloxy-3-triphenylmethyloxy-(1S)-propyl]-5-(1-ethynyl-2,2-dimethyl)-(4R,5R)-1,3-dioxolane
CAS No.:385810-28-6
Molecular Formula:C₃₅H₄₄O₄Si
Molecular Weight:556.817
Hs Code.:

Synonyms:4-[1-tert-butyldimethylsilyloxy-3-triphenylmethyloxy-(1S)-propyl]-5-(1-ethynyl-2,2-dimethyl)-(4R,5R)-1,3-dioxolane

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Chemical Property of 4-[1-tert-butyldimethylsilyloxy-3-triphenylmethyloxy-(1S)-propyl]-5-(1-ethynyl-2,2-dimethyl)-(4R,5R)-1,3-dioxolane

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Technology Process of 4-[1-tert-butyldimethylsilyloxy-3-triphenylmethyloxy-(1S)-propyl]-5-(1-ethynyl-2,2-dimethyl)-(4R,5R)-1,3-dioxolane

There total 5 articles about 4-[1-tert-butyldimethylsilyloxy-3-triphenylmethyloxy-(1S)-propyl]-5-(1-ethynyl-2,2-dimethyl)-(4R,5R)-1,3-dioxolane 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: 56.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 385810-27-5
1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-3-triphenylmethyloxy-(1S)-propan-1-ol

: 385810-28-6
4-[1-tert-butyldimethylsilyloxy-3-triphenylmethyloxy-(1S)-propyl]-5-(1-ethynyl-2,2-dimethyl)-(4R,5R)-1,3-dioxolane

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1021/jo010455m

Reference yield:

: 55797-78-9
ethyl 2-{(3aS,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}acetate

: 385810-28-6
4-[1-tert-butyldimethylsilyloxy-3-triphenylmethyloxy-(1S)-propyl]-5-(1-ethynyl-2,2-dimethyl)-(4R,5R)-1,3-dioxolane

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / CCl₄; PPh₃ / 6 h / Heating

2: 90 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

3: 91 percent / LiNH₂; liquid NH₃ / tetrahydrofuran / 1 h

4: 90 percent / et3N / CH₂Cl₂ / 1 h / 20 °C

5: 56 percent / imidazole / CH₂Cl₂ / 48 h / 20 °C

With 1H-imidazole; tetrachloromethane; lithium aluminium tetrahydride; lithium amide; ammonia; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo010455m

Reference yield:

: 385810-26-4
1-[5-(1-ethynyl)-2,2-dimethyl-(4S,5R)-1,3-dioxolan-4-yl]-(1S)-propane-1,3-diol

: 385810-28-6
4-[1-tert-butyldimethylsilyloxy-3-triphenylmethyloxy-(1S)-propyl]-5-(1-ethynyl-2,2-dimethyl)-(4R,5R)-1,3-dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / et3N / CH₂Cl₂ / 1 h / 20 °C

2: 56 percent / imidazole / CH₂Cl₂ / 48 h / 20 °C

With 1H-imidazole; triethylamine; In dichloromethane;
DOI:10.1021/jo010455m