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

Base Information

• Chemical Name: (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3-methyl ester
• CAS No.: 144568-98-9
• Molecular Formula: C₃₄H₄₆O₁₃
• Molecular Weight: 662.731

Synonyms:

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

Chemical Property:

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

There total 1 articles about (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3-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:

methanol (67-56-1) + zaragozic acid A (138682-84-5,144786-97-0,146075-86-7,148152-80-1,149656-40-6,142561-96-4) → (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3-methyl ester (144568-98-9)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 48h; Yield given;

DOI:10.1039/a704363e

Reference yield:

(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3-methyl ester (144568-98-9) → (1S,3S,4S,5R,6R,7R)-7-Acetoxy-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4,5-di-tert-butyl ester 3-methyl ester (202195-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 3 h / 80 °C

2: 54 percent / Et₃N / CH₂Cl₂ / 20 h / 20 °C

With triethylamine; In dichloromethane; toluene;

DOI:10.1039/a704363e

Reference yield:

(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3-methyl ester (144568-98-9) → (1S,3S,4S,5R,6R,7R)-7-Acetoxy-1-((4S,5R)-4-acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 4,5-di-tert-butyl ester 3-methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 3 h / 80 °C

2: 14 percent / Et₃N / CH₂Cl₂ / 20 h / 20 °C

With triethylamine; In dichloromethane; toluene;

DOI:10.1039/a704363e

upstream raw materials:

methanol

zaragozic acid A

Downstream raw materials:

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

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