9R-O-chloroacetyl-6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A₁

Base Information

• Chemical Name: 9R-O-chloroacetyl-6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A₁
• CAS No.: 139746-47-7
• Molecular Formula: C₃₃H₄₇ClO₁₀
• Molecular Weight: 639.183

Synonyms:9R-O-chloroacetyl-6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A₁

Chemical Property of 9R-O-chloroacetyl-6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A₁

Chemical Property:

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Technology Process of 9R-O-chloroacetyl-6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A₁

There total 5 articles about 9R-O-chloroacetyl-6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A₁ 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: 88.6%

6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A1 (124781-27-7) + Chloroacetic anhydride (541-88-8) → 9R-O-chloroacetyl-6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A1 (139746-47-7)

Guidance literature:

With dmap; In pyridine; dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.39.2819

Reference yield:

6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide (124781-20-0) → 9R-O-chloroacetyl-6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A1 (139746-47-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / 10-camphorsulfonic acid (CSA) / methanol / 0.5 h / Ambient temperature

2: 56 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 20.5 h / Ambient temperature

3: 94 percent / pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂ / 0.08 h / Ambient temperature

4: 100 percent / NaBH₄ / methanol / 0.17 h / 0 °C

5: 88.6 percent / DMAP / pyridine; CH₂Cl₂ / 0.5 h / Ambient temperature

With dmap; sodium tetrahydroborate; (1S)-10-camphorsulfonic acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In pyridine; methanol; dichloromethane;

DOI:10.1248/cpb.39.2819

Reference yield:

6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)niddanolide (124781-26-6) → 9R-O-chloroacetyl-6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A1 (139746-47-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaBH₄ / methanol / 0.17 h / 0 °C

2: 88.6 percent / DMAP / pyridine; CH₂Cl₂ / 0.5 h / Ambient temperature

With dmap; sodium tetrahydroborate; In pyridine; methanol; dichloromethane;

DOI:10.1248/cpb.39.2819

upstream raw materials:

6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)leuconolide A₁

Chloroacetic anhydride

6-dihydro-6-O-(4-methoxybenzyl)-3,5-O-isopropylideneniddanolide

6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(4-methoxybenzyl)niddanolide

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