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

Base Information

• Chemical Name: 6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(tert-butyldiphenylsilyl)niddanolide
• CAS No.: 137787-94-1
• Molecular Formula: C₃₉H₅₄O₈Si
• Molecular Weight: 678.938

Synonyms:6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(tert-butyldiphenylsilyl)niddanolide

Chemical Property of 6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(tert-butyldiphenylsilyl)niddanolide

Chemical Property:

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Technology Process of 6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(tert-butyldiphenylsilyl)niddanolide

There total 2 articles about 6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(tert-butyldiphenylsilyl)niddanolide 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: 84.0%

2-Methoxypropene (116-11-0) + 6''-dihydro-12S,13R-epoxy-6''-O-(tert-butyldiphenylsilyl)niddanolide (143317-68-4) → 6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(tert-butyldiphenylsilyl)niddanolide (137787-94-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 0.333333h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81225-4

Reference yield:

(11E,13E)-(4R,5S,6S,7R,9R,16R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,6-dihydroxy-5-methoxy-9,16-dimethyl-oxacyclohexadeca-11,13-diene-2,10-dione (77405-60-8) → 6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(tert-butyldiphenylsilyl)niddanolide (137787-94-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / mCPBA, NaHCO₃ / CH₂Cl₂ / 23 h / Ambient temperature

2: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.33 h / Ambient temperature

With pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)81225-4

Reference yield: 100.0%

6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(tert-butyldiphenylsilyl)niddanolide (137787-94-1) → 6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(tert-butyldiphenyl)leuconolide A1 (137787-95-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 0.166667h; Ambient temperature; other substrate;

DOI:10.1016/S0040-4020(01)81225-4

upstream raw materials:

2-Methoxypropene

6''-dihydro-12S,13R-epoxy-6''-O-(tert-butyldiphenylsilyl)niddanolide

(11E,13E)-(4R,5S,6S,7R,9R,16R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,6-dihydroxy-5-methoxy-9,16-dimethyl-oxacyclohexadeca-11,13-diene-2,10-dione

Downstream raw materials:

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

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