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

Base Information

• Chemical Name: 4-[1-azido-5-benzyloxy-(1S)-pentyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4S,5R)-1,3-dioxolane
• CAS No.: 678156-16-6
• Molecular Formula: C₂₅H₃₃N₃O₄S
• Molecular Weight: 471.621

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

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

Chemical Property:

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

There total 10 articles about 4-[1-azido-5-benzyloxy-(1S)-pentyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4S,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: 87.0%

2,2-dimethoxy-propane (77-76-9) + 4-azido-8-benzyloxy-1-(SS)-(4-methylphenylsulfinyl)-(2R,3S,4S)-octane-2,3-diol (678156-15-5) → 4-[1-azido-5-benzyloxy-(1S)-pentyl]-2,2-dimethyl-5-(SS)-(4-methylphenylsulfinylmethyl)-(4S,5R)-1,3-dioxolane (678156-16-6)

Guidance literature:

With camphor-10-sulfonic acid; In acetone; at 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2003.12.017

Reference yield:

1 ,5-pentanediol (111-29-5) → 4-[1-azido-5-benzyloxy-(1S)-pentyl]-2,2-dimethyl-5-(SS)-(4-methylphenylsulfinylmethyl)-(4S,5R)-1,3-dioxolane (678156-16-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 80 percent / NaH

2.1: 80 percent / PCC

3.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 70 percent / tetrahydrofuran; hexane / 3 h / -78 °C

4.1: 91 percent / ZnCl₂; DIBAL-H / tetrahydrofuran; toluene / 0.67 h / -78 °C

5.1: 85 percent / H₂O; N-bromosuccinimide / toluene / 0.25 h / 20 °C

6.1: 83 percent / K₂CO₃ / methanol / 1.75 h / 0 - 20 °C

7.1: 85 percent / NH₄Cl; NaN₃ / methanol; H₂O / 6 h / Heating

8.1: 87 percent / CSA / acetone / 1 h / 20 °C

With N-Bromosuccinimide; sodium azide; camphor-10-sulfonic acid; water; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; pyridinium chlorochromate; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; water; acetone; toluene;

DOI:10.1016/j.tetasy.2003.12.017

Reference yield:

5-(benzyloxy)-1-pentanol (4541-15-5) → 4-[1-azido-5-benzyloxy-(1S)-pentyl]-2,2-dimethyl-5-(SS)-(4-methylphenylsulfinylmethyl)-(4S,5R)-1,3-dioxolane (678156-16-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 80 percent / PCC

2.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 70 percent / tetrahydrofuran; hexane / 3 h / -78 °C

3.1: 91 percent / ZnCl₂; DIBAL-H / tetrahydrofuran; toluene / 0.67 h / -78 °C

4.1: 85 percent / H₂O; N-bromosuccinimide / toluene / 0.25 h / 20 °C

5.1: 83 percent / K₂CO₃ / methanol / 1.75 h / 0 - 20 °C

6.1: 85 percent / NH₄Cl; NaN₃ / methanol; H₂O / 6 h / Heating

7.1: 87 percent / CSA / acetone / 1 h / 20 °C

With N-Bromosuccinimide; sodium azide; camphor-10-sulfonic acid; water; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; pyridinium chlorochromate; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; water; acetone; toluene;

DOI:10.1016/j.tetasy.2003.12.017

upstream raw materials:

2,2-dimethoxy-propane

4-azido-8-benzyloxy-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3S,4S)-octane-2,3-diol

1 ,5-pentanediol

5-(benzyloxy)-1-pentanol

Downstream raw materials:

(+)-lentiginosine

5-[1-azido-5-benzyloxy-(1S)-pentyl]-2,2-dimethyl-(4S,5S)-1,3-dioxolan-4-ylmethanol

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