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

Base Information

• Chemical Name: <1S-<1α-(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-carbamoyl-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 4,5-dimethyl ester
• CAS No.: 152997-52-9
• Molecular Formula: C₃₇H₅₁NO₁₃
• Molecular Weight: 717.811

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

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

Chemical Property:

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

There total 2 articles about <1S-<1α-(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-carbamoyl-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 4,5-dimethyl ester 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:

zaragozic acid A trimethyl ester (142561-97-5) → <1S-<1α-(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-carbamoyl-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 4,5-dimethyl ester (152997-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / tetrahydrofuran / 21 h

2: 1.) oxalyl chloride, 3.) NH₃ / 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) CH₂Cl₂, THF, acetonitrile, a) 0 deg C, 2 h, b) 21 deg C, 2 h

With sodium hydroxide; oxalyl dichloride; ammonia; In tetrahydrofuran;

DOI:10.1021/jm00018a010

Reference yield:

<1S-<1α-(4R*,5S*),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-6-octenoate), 4,5-dimethyl ester (144548-73-2) → <1S-<1α-(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-carbamoyl-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 4,5-dimethyl ester (152997-52-9)

Guidance literature:

With oxalyl dichloride; ammonia; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) CH₂Cl₂, THF, acetonitrile, a) 0 deg C, 2 h, b) 21 deg C, 2 h;

DOI:10.1021/jm00018a010

Reference yield: 85.0%

<1S-<1α-(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-carbamoyl-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 4,5-dimethyl ester (152997-52-9) → <1S-<1α-(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-cyano-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 4,5-dimethyl ester (152997-53-0)

Guidance literature:

With triethylamine; trifluoroacetic anhydride; In dichloromethane; at 21 ℃; for 5h;

DOI:10.1021/jm00018a010

upstream raw materials:

<1S-<1α-(4R*,5S*),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-6-octenoate), 4,5-dimethyl ester

zaragozic acid A trimethyl ester

Downstream raw materials:

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

<1S-<1α(4R*,5S*),3α,4β,5α,6α,7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-4,6,7-trihydroxy-3-(1-methyl-1H-tetrazol-5-yl)-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 4-methyl ester

(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,6,7-trihydroxy-3-(1-methyl-1H-tetrazol-5-yl)-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid dimethyl ester

(1S,3R,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)-4,7-dihydroxy-3-(1H-tetrazol-5-yl)-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid

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