<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

Base Information

Chemical Name:<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
CAS No.:152997-67-6
Molecular Formula:C₂₇H₃₄N₄O₁₁
Molecular Weight:590.587
Hs Code.:

<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

Synonyms:<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

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Chemical Property of <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

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Technology Process of <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

There total 7 articles about <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 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: 7.0%

: 152997-66-5
(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

: 152997-67-6
<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

Guidance literature:: With 2,4,6-trimethyl-pyridine; lithium iodide; at 45 - 50 ℃; for 45h;
DOI:10.1021/jm00018a010

Reference yield:

: 142561-97-5
zaragozic acid A trimethyl ester

: 152997-67-6
<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

Guidance literature:: Multi-step reaction with 7 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

3: 85 percent / triethylamine, trifluoroacetic anhydride / CH₂Cl₂ / 5 h / 21 °C

4: NaN₃, Et₃N*HCl / dimethylformamide / 2 h / 120 °C

5: NaHCO₃ / dimethylformamide / 16 h

6: N-methylhydroxylamine hydrochloride, triethylamine / dimethylformamide / 18 h / 21 °C

7: 7 percent / 2,4,6-collidine, LiI / 45 h / 45 - 50 °C

With 2,4,6-trimethyl-pyridine; sodium hydroxide; sodium azide; oxalyl dichloride; N-methylhydroxyamine hydrochloride; ammonia; triethylamine hydrochloride; sodium hydrogencarbonate; triethylamine; trifluoroacetic anhydride; lithium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00018a010

Reference yield:

: 144548-73-2
<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

: 152997-67-6
<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

Guidance literature:: Multi-step reaction with 6 steps

1: 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

2: 85 percent / triethylamine, trifluoroacetic anhydride / CH₂Cl₂ / 5 h / 21 °C

3: NaN₃, Et₃N*HCl / dimethylformamide / 2 h / 120 °C

4: NaHCO₃ / dimethylformamide / 16 h

5: N-methylhydroxylamine hydrochloride, triethylamine / dimethylformamide / 18 h / 21 °C

6: 7 percent / 2,4,6-collidine, LiI / 45 h / 45 - 50 °C

With 2,4,6-trimethyl-pyridine; sodium azide; oxalyl dichloride; N-methylhydroxyamine hydrochloride; ammonia; triethylamine hydrochloride; sodium hydrogencarbonate; triethylamine; trifluoroacetic anhydride; lithium iodide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00018a010