(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-(tert-butyl-dimethyl-silanyloxy)-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

Base Information

• Chemical Name: (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-(tert-butyl-dimethyl-silanyloxy)-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
• CAS No.: 152997-54-1
• Molecular Formula: C₄₉H₇₆O₁₄Si
• Molecular Weight: 917.22

Synonyms:(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-(tert-butyl-dimethyl-silanyloxy)-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

Chemical Property of (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-(tert-butyl-dimethyl-silanyloxy)-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

Chemical Property:

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Technology Process of (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-(tert-butyl-dimethyl-silanyloxy)-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

There total 4 articles about (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-(tert-butyl-dimethyl-silanyloxy)-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 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: 98.0%

C50H78O14Si (152997-74-5) → (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-(tert-butyl-dimethyl-silanyloxy)-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 (152997-54-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1021/jm950893j

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-(tert-butyl-dimethyl-silanyloxy)-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 (152997-54-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / imidazole / dimethylformamide / 16.5 h / 65 °C

2: 98 percent / 0.1 M sodium hydroxide / tetrahydrofuran / 0.5 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

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,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-(tert-butyl-dimethyl-silanyloxy)-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 (152997-54-1)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; hydrogenchloride; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm950893j

upstream raw materials:

C₅₀H₇₈O₁₄Si

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

C₄₉H₇₈O₁₃Si

(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

(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

(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

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