<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(5-methyl-3-methylene-4(n-propionyloxy)-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

Base Information

• Chemical Name: <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(5-methyl-3-methylene-4(n-propionyloxy)-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate)
• CAS No.: 146007-82-1
• Molecular Formula: C₃₆H₄₈O₁₄
• Molecular Weight: 704.769

Synonyms:<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(5-methyl-3-methylene-4(n-propionyloxy)-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

Chemical Property of <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(5-methyl-3-methylene-4(n-propionyloxy)-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

Chemical Property:

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Technology Process of <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(5-methyl-3-methylene-4(n-propionyloxy)-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

There total 4 articles about <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(5-methyl-3-methylene-4(n-propionyloxy)-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate) 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: 98.0%

(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester (146968-13-0) → <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(5-methyl-3-methylene-4(n-propionyloxy)-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate) (146007-82-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; Ambient temperature;

DOI:10.1021/jm00049a022

Reference yield:

<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester (144358-24-7) → <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(5-methyl-3-methylene-4(n-propionyloxy)-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate) (146007-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

2: cerium(III) chloride, ethylmagnesium chloride / tetrahydrofuran / 0.83 h / -78 °C

3: 73 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

4: 98 percent / TFA / CH₂Cl₂ / Ambient temperature

With dmap; cerium(III) chloride; ethylmagnesium chloride; pyridinium p-toluenesulfonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00049a022

Reference yield:

<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(4-hydroxy-5-methyl-3-methylene-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate) 7-(1-methoxy-1-methylethyl ether) ester (146968-12-9) → <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(5-methyl-3-methylene-4(n-propionyloxy)-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate) (146007-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: 98 percent / TFA / CH₂Cl₂ / Ambient temperature

With dmap; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm00049a022

upstream raw materials:

(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-1-((4S,5R)-5-methyl-3-methylene-6-phenyl-4-propionyloxy-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester

<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-(4-hydroxy-5-methyl-3-methylene-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate) 7-(1-methoxy-1-methylethyl ether) ester

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

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