(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid

Base Information

• Chemical Name: (1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid
• CAS No.: 153430-99-0
• Molecular Formula: C₃₅H₄₉NO₁₂
• Molecular Weight: 675.774
• Mol file: 153430-99-0.mol

Synonyms:(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid

Chemical Property of (1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid

There total 9 articles about (1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid 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: 38.0%

(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid di-tert-butyl ester (153430-95-6) → (1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid (153430-99-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 4h; Ambient temperature;

DOI:10.1021/jm950893j

Reference yield:

zaragozic acid A (138682-84-5,144786-97-0,146075-86-7,148152-80-1,149656-40-6,142561-96-4) → (1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid (153430-99-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) conc. hydrochloric acid / 1.) methanol, RT, 24 h, 2.) toluene, 80 deg C, 3.25 h

2: 76 percent / imidazole / dimethylformamide / 16.5 h / 65 °C

3: 98 percent / 0.1 M sodium hydroxide / tetrahydrofuran / 0.5 h / Ambient temperature

4: 1.) N-hydroxysuccinimide, N,N-dicyclohexylcarbodiimide, 2.) sodium borohydride / 1.) THF, RT, 17 h, 2.) DMF, RT, 55 min

5: 95 percent / 2,4,6-collidine / CH₂Cl₂ / 0.75 h

6: 91 percent / sodium azide / dimethylformamide / 4 h / 20 °C

7: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.17 h / Ambient temperature

8: 66 percent / triphenylphosphine / tetrahydrofuran; H₂O / 23 h / 44 °C

9: 38 percent / 6,5 M hydrogen chloride / dioxane / 4 h / Ambient temperature

With 1H-imidazole; 2,4,6-trimethyl-pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; sodium azide; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm950893j

Reference yield:

(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-azidomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid di-tert-butyl ester (153430-94-5) → (1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid (153430-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / triphenylphosphine / tetrahydrofuran; H₂O / 23 h / 44 °C

2: 38 percent / 6,5 M hydrogen chloride / dioxane / 4 h / Ambient temperature

With hydrogenchloride; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/jm950893j

upstream raw materials:

(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-aminomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid di-tert-butyl ester

zaragozic acid A

(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)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4,5-di-tert-butyl ester 3-methyl ester

(1S,3R,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-3-azidomethyl-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid di-tert-butyl ester

Downstream 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-ureidomethyl-2,8-dioxa-bicyclo[3.2.1]octane-4,5-dicarboxylic acid