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

Base Information

Chemical Name:(4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-(4-methylphenylsulfinylmethyl)-1,3-dioxolane
CAS No.:609811-96-3
Molecular Formula:C₂₂H₂₇N₃O₄S
Molecular Weight:429.54
Hs Code.:

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

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

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

There total 5 articles about (4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-(4-methylphenylsulfinylmethyl)-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: 87.0%

: 77-76-9
2,2-dimethoxy-propane

: 609811-95-2
(2S,3R,4R)-4-azido-5-benzyloxy-1-(4-methylphenylsulfinyl)pentane-2,3-diol

: 609811-96-3
(4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-(4-methylphenylsulfinylmethyl)-1,3-dioxolane

Guidance literature:: With camphor-10-sulfonic acid; In acetone; at 20 ℃; for 1h;
DOI:10.1021/jo034157w

Reference yield:

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

: 609811-96-3
(4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-(4-methylphenylsulfinylmethyl)-1,3-dioxolane

Guidance literature:: Multi-step reaction with 4 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

With N-Bromosuccinimide; sodium azide; camphor-10-sulfonic acid; water; potassium carbonate; ammonium chloride; In methanol; water; acetone; toluene;
DOI:10.1021/jo034157w

Reference yield:

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

: 609811-96-3
(4R,5S)-4-[(1R)-1-azido-2-(benzyloxy)ethyl]-2,2-dimethyl-5-(4-methylphenylsulfinylmethyl)-1,3-dioxolane

Guidance literature:: Multi-step reaction with 5 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

With N-Bromosuccinimide; sodium azide; camphor-10-sulfonic acid; water; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; In tetrahydrofuran; methanol; water; acetone; toluene;
DOI:10.1021/jo034157w