(4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)-3-tetradecenyl]-1,3-dioxolane

Base Information

Chemical Name:(4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)-3-tetradecenyl]-1,3-dioxolane
CAS No.:609812-01-3
Molecular Formula:C₃₅H₅₁N₃O₅S
Molecular Weight:625.873
Hs Code.:

Synonyms:(4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)-3-tetradecenyl]-1,3-dioxolane

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Chemical Property of (4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)-3-tetradecenyl]-1,3-dioxolane

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Technology Process of (4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)-3-tetradecenyl]-1,3-dioxolane

There total 8 articles about (4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)-3-tetradecenyl]-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: 82.0%

: 609811-98-5
2-azido-2-[(4R,5S)-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfanyl)-3-tetradecenyl]-1,3-dioxolan-4-yl]ethyl benzyl ether

: 609812-01-3
(4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)-3-tetradecenyl]-1,3-dioxolane

Guidance literature:: With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; In tetrahydrofuran; methanol; water; at 0 - 20 ℃; for 4.5h;
DOI:10.1021/jo034157w

Reference yield:

: 110426-21-6
(E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one

: 609812-01-3
(4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)-3-tetradecenyl]-1,3-dioxolane

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / DIBAL-H / tetrahydrofuran; toluene / 0.58 h / -78 °C

2: 88 percent / N-bromosuccinimide; water / toluene / 0.25 h / 20 °C

3: 83 percent / K₂CO₃ / methanol / 1.75 h / 0 - 20 °C

4: 85 percent / NaN₃; NH₄Cl / methanol; H₂O / 6 h / Heating

5: 87 percent / CSA / acetone / 1 h / 20 °C

6: 1-tridecene / CH₂Cl₂ / 1.08 h / 0 °C

7: 930 mg / SnCl₄ / CH₂Cl₂ / 0.17 h / 0 °C

8: 82 percent / 2KHSO₅*KHSO₄*K₂SO₄ / tetrahydrofuran; methanol; H₂O / 4.5 h / 0 - 20 °C

With potassium sulfate; potassium hydrogensulfate; N-Bromosuccinimide; potassium peroxomonosulfate; sodium azide; 1-tridecene; camphor-10-sulfonic acid; water; tin(IV) chloride; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 6: Pummerer reaction;
DOI:10.1021/jo034157w

Reference yield:

: 110426-22-7
(2S,3E)-5-benzyloxy-1-(4-methylphenylsulfinyl)-3-penten-2-ol

: 609812-01-3
(4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(E)-1-(4-methylphenylsulfonyl)-3-tetradecenyl]-1,3-dioxolane

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / N-bromosuccinimide; water / toluene / 0.25 h / 20 °C

2: 83 percent / K₂CO₃ / methanol / 1.75 h / 0 - 20 °C

3: 85 percent / NaN₃; NH₄Cl / methanol; H₂O / 6 h / Heating

4: 87 percent / CSA / acetone / 1 h / 20 °C

5: 1-tridecene / CH₂Cl₂ / 1.08 h / 0 °C

6: 930 mg / SnCl₄ / CH₂Cl₂ / 0.17 h / 0 °C

7: 82 percent / 2KHSO₅*KHSO₄*K₂SO₄ / tetrahydrofuran; methanol; H₂O / 4.5 h / 0 - 20 °C

With potassium sulfate; potassium hydrogensulfate; N-Bromosuccinimide; potassium peroxomonosulfate; sodium azide; 1-tridecene; camphor-10-sulfonic acid; water; tin(IV) chloride; potassium carbonate; ammonium chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 5: Pummerer reaction;
DOI:10.1021/jo034157w