(1R,2S,5R,7S,8R,9R)-7-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-9-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-8-hydroxy-3,6,10-trioxa-tricyclo[5.2.1.0^2,5]decane-1,2-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (1R,2S,5R,7S,8R,9R)-7-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-9-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-8-hydroxy-3,6,10-trioxa-tricyclo[5.2.1.0^2,5]decane-1,2-dicarboxylic acid dimethyl ester
• CAS No.: 310903-05-0
• Molecular Formula: C₃₇H₅₀O₁₂
• Molecular Weight: 686.797
• Mol file: 310903-05-0.mol

Synonyms:

Chemical Property of (1R,2S,5R,7S,8R,9R)-7-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-9-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-8-hydroxy-3,6,10-trioxa-tricyclo[5.2.1.0^2,5]decane-1,2-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5R,7S,8R,9R)-7-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-9-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-8-hydroxy-3,6,10-trioxa-tricyclo[5.2.1.0^2,5]decane-1,2-dicarboxylic acid dimethyl ester

There total 6 articles about (1R,2S,5R,7S,8R,9R)-7-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-9-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-8-hydroxy-3,6,10-trioxa-tricyclo[5.2.1.0^2,5]decane-1,2-dicarboxylic acid 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: 37.0%

(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-(toluene-4-sulfonyloxymethyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid dimethyl ester (310903-04-9) → (1R,2S,5R,7S,8R,9R)-7-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-9-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-8-hydroxy-3,6,10-trioxa-tricyclo[5.2.1.02,5]decane-1,2-dicarboxylic acid dimethyl ester (310903-05-0)

Guidance literature:

With tri-n-butyl-tin hydride; sodium iodide;

DOI:10.1016/S0040-4039(00)01286-7

Reference yield:

zaragozic acid A (138682-84-5,144786-97-0,146075-86-7,148152-80-1,149656-40-6,142561-96-4) → (1R,2S,5R,7S,8R,9R)-7-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-9-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-8-hydroxy-3,6,10-trioxa-tricyclo[5.2.1.02,5]decane-1,2-dicarboxylic acid dimethyl ester (310903-05-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 90 percent / NaHCO₃ / dimethylformamide

2.1: 100 percent / aq. NAOH / tetrahydrofuran

3.1: N-hydroxysuccinimide; 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-Ts / tetrahydrofuran

3.2: 55 percent / NaBH₄ / tetrahydrofuran

4.1: 70 percent / pyridine / CH₂Cl₂

5.1: 37 percent / Bu₃SnH; NaI

With pyridine; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; tri-n-butyl-tin hydride; N-cyclohexyl-N'-β-(4-methylmorpholinium)ethylcarbodiimide p-toluenesulfonate; sodium hydrogencarbonate; sodium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Esterification / 2.1: Hydrolysis / 3.1: Substitution / 3.2: Reduction / 4.1: Tosylation / 5.1: Condensation;

DOI:10.1016/S0040-4039(00)01286-7

Reference yield:

zaragozic acid A trimethyl ester (142561-97-5) → (1R,2S,5R,7S,8R,9R)-7-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-9-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-8-hydroxy-3,6,10-trioxa-tricyclo[5.2.1.02,5]decane-1,2-dicarboxylic acid dimethyl ester (310903-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / aq. NAOH / tetrahydrofuran

2.1: N-hydroxysuccinimide; 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-Ts / tetrahydrofuran

2.2: 55 percent / NaBH₄ / tetrahydrofuran

3.1: 70 percent / pyridine / CH₂Cl₂

4.1: 37 percent / Bu₃SnH; NaI

With pyridine; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; tri-n-butyl-tin hydride; N-cyclohexyl-N'-β-(4-methylmorpholinium)ethylcarbodiimide p-toluenesulfonate; sodium iodide; In tetrahydrofuran; dichloromethane; 1.1: Hydrolysis / 2.1: Substitution / 2.2: Reduction / 3.1: Tosylation / 4.1: Condensation;

DOI:10.1016/S0040-4039(00)01286-7

upstream raw materials:

(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-(toluene-4-sulfonyloxymethyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid dimethyl ester

zaragozic acid A trimethyl ester

zaragozic acid A

<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