(4S)-4-{(S)-azido [1-(benzyloxy)cyclopropyl]methyl}-2,2-dimethyl-1,3-dioxolane

Base Information

Chemical Name:(4S)-4-{(S)-azido [1-(benzyloxy)cyclopropyl]methyl}-2,2-dimethyl-1,3-dioxolane
CAS No.:287205-36-1
Molecular Formula:C₁₆H₂₁N₃O₃
Molecular Weight:303.361
Hs Code.:

Synonyms:(4S)-4-{(S)-azido [1-(benzyloxy)cyclopropyl]methyl}-2,2-dimethyl-1,3-dioxolane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S)-4-{(S)-azido [1-(benzyloxy)cyclopropyl]methyl}-2,2-dimethyl-1,3-dioxolane

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Technology Process of (4S)-4-{(S)-azido [1-(benzyloxy)cyclopropyl]methyl}-2,2-dimethyl-1,3-dioxolane

There total 4 articles about (4S)-4-{(S)-azido [1-(benzyloxy)cyclopropyl]methyl}-2,2-dimethyl-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: 50.0%

: 100-39-0
benzyl bromide

: 287205-35-0
1-{(S)-azido [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}cyclopropanol

: 287205-36-1
(4S)-4-{(S)-azido [1-(benzyloxy)cyclopropyl]methyl}-2,2-dimethyl-1,3-dioxolane

Guidance literature:: With 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 50 ℃; for 18h;
DOI:10.1016/S0040-4020(00)00369-0

Reference yield:

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 287205-36-1
(4S)-4-{(S)-azido [1-(benzyloxy)cyclopropyl]methyl}-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 6 h / 70 °C

1.2: 70 percent / TDA-1 / tetrahydrofuran / 14 h / 70 °C

2.1: 49 percent / m-CPBA / CH₂Cl₂ / 0 - 20 °C

3.1: 74 percent / NaN₃; H₂O; NH₄Cl / methanol / 12 h / 80 °C

4.1: 50 percent / NaH; n-Bu₄NI; imidazole / tetrahydrofuran / 18 h / 50 °C

With 1H-imidazole; sodium azide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; 1.1: Dehydrobromination / 1.2: Wittig reaction / 2.1: Epoxidation / 3.1: Ring cleavage / 4.1: Etherification;
DOI:10.1016/S0040-4020(00)00369-0

Reference yield:

: 287205-32-7
(S)-4-cyclopropylidene-2,2-dimethyl-1,3-dioxolane

: 287205-36-1
(4S)-4-{(S)-azido [1-(benzyloxy)cyclopropyl]methyl}-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 3 steps

1: 49 percent / m-CPBA / CH₂Cl₂ / 0 - 20 °C

2: 74 percent / NaN₃; H₂O; NH₄Cl / methanol / 12 h / 80 °C

3: 50 percent / NaH; n-Bu₄NI; imidazole / tetrahydrofuran / 18 h / 50 °C

With 1H-imidazole; sodium azide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; 1: Epoxidation / 2: Ring cleavage / 3: Etherification;
DOI:10.1016/S0040-4020(00)00369-0