(3S,4aS,5S,6S,7S,11S,12aS)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecene-3,5,7,11-tetrol 5-acetate

Base Information

• Chemical Name: (3S,4aS,5S,6S,7S,11S,12aS)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecene-3,5,7,11-tetrol 5-acetate
• CAS No.: 849705-68-6
• Molecular Formula: C₂₂H₃₄O₅
• Molecular Weight: 378.509

Synonyms:(3S,4aS,5S,6S,7S,11S,12aS)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecene-3,5,7,11-tetrol 5-acetate

Chemical Property of (3S,4aS,5S,6S,7S,11S,12aS)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecene-3,5,7,11-tetrol 5-acetate

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Technology Process of (3S,4aS,5S,6S,7S,11S,12aS)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecene-3,5,7,11-tetrol 5-acetate

There total 2 articles about (3S,4aS,5S,6S,7S,11S,12aS)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecene-3,5,7,11-tetrol 5-acetate 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: 60.0%

taxuyunnanin C (156127-34-3) → 10β-hydroxy-2α,5α14β-triacetoxytaxa-4(20),11(12)-diene (157056-97-8) + (3S,4aS,5S,6S,7S,11S,12aS)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecene-3,5,7,11-tetrol 5-acetate (849705-68-6) + 10β,14β-dihydroxy-2α,5α-diacetoxy-4(20),11-taxadiene (167355-42-2)

Guidance literature:

With sodium hydroxide; In methanol; at 30 ℃;

DOI:10.1016/S0031-9422(98)00674-8

Reference yield:

taxuyunnanin C (156127-34-3) → 2,10,14-desacetyl taxuyunnanine C (176590-75-3) + 10β-hydroxy-2α,5α14β-triacetoxytaxa-4(20),11(12)-diene (157056-97-8) + 2α,5α,10β,14β-tetrahydroxytaxa-4(20),11-diene (444578-19-2) + (3S,4aS,5S,6S,7S,11S,12aS)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecene-3,5,7,11-tetrol 5-acetate (849705-68-6) + 10β,14β-dihydroxy-2α,5α-diacetoxy-4(20),11-taxadiene (167355-42-2) + 2,14-desacetyl taxuyunnanine C

Guidance literature:

With sodium hydroxide; In methanol; at 30 ℃; kinetics plots of desacetylation; effect of NaOH conc.;

DOI:10.1016/S0031-9422(98)00674-8

Reference yield:

acetylcoenzyme A (72-89-9) + (3S,4aS,5S,6S,7S,11S,12aS)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecene-3,5,7,11-tetrol 5-acetate (849705-68-6) → taxuyunnanin C (156127-34-3)

Guidance literature:

In dimethyl sulfoxide; at 35 ℃; for 0.5h; pH 8.5-9.0; rate of acetylation in presence 10-hydroxytaxane O-acetyltransferase (from cell suspension cultures of Taxus chinensis);

DOI:10.1016/S0031-9422(98)00674-8

upstream raw materials:

taxuyunnanin C

Downstream raw materials:

taxuyunnanin C

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