(E)-(4S,7R)-7-Hydroxy-4-(4-methoxy-benzyloxy)-oct-2-enoic acid (E)-(1R,2S)-2-allyloxy-4-carboxy-1-methyl-but-3-enyl ester

Base Information

• Chemical Name: (E)-(4S,7R)-7-Hydroxy-4-(4-methoxy-benzyloxy)-oct-2-enoic acid (E)-(1R,2S)-2-allyloxy-4-carboxy-1-methyl-but-3-enyl ester
• CAS No.: 161200-14-2
• Molecular Formula: C₂₅H₃₄O₈
• Molecular Weight: 462.54
• Mol file: 161200-14-2.mol

Synonyms:

Chemical Property of (E)-(4S,7R)-7-Hydroxy-4-(4-methoxy-benzyloxy)-oct-2-enoic acid (E)-(1R,2S)-2-allyloxy-4-carboxy-1-methyl-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4S,7R)-7-Hydroxy-4-(4-methoxy-benzyloxy)-oct-2-enoic acid (E)-(1R,2S)-2-allyloxy-4-carboxy-1-methyl-but-3-enyl ester

There total 9 articles about (E)-(4S,7R)-7-Hydroxy-4-(4-methoxy-benzyloxy)-oct-2-enoic acid (E)-(1R,2S)-2-allyloxy-4-carboxy-1-methyl-but-3-enyl 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:

(E)-(4S,7R)-7-Hydroxy-4-(4-methoxy-benzyloxy)-oct-2-enoic acid (E)-(1R,2S)-2-allyloxy-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester (161200-10-8) → (E)-(4S,7R)-7-Hydroxy-4-(4-methoxy-benzyloxy)-oct-2-enoic acid (E)-(1R,2S)-2-allyloxy-4-carboxy-1-methyl-but-3-enyl ester (161200-14-2)

Guidance literature:

With 2,6-dichloro-benzonitrile; In benzene; Yield given; Ambient temperature;

DOI:10.1016/0040-4039(94)02196-I

Reference yield:

Formic acid (1R,2R)-2-allyloxy-1-methyl-3-oxo-propyl ester (161200-08-4) → (E)-(4S,7R)-7-Hydroxy-4-(4-methoxy-benzyloxy)-oct-2-enoic acid (E)-(1R,2S)-2-allyloxy-4-carboxy-1-methyl-but-3-enyl ester (161200-14-2)

Guidance literature:

Multi-step reaction with 5 steps

1: benzene / 80 °C

2: 92 percent / 2 percent HCl / dioxane; H₂O

3: DMAP / toluene / Ambient temperature

4: conc. HCl / methanol; ethyl acetate

5: DBN / benzene / Ambient temperature

With hydrogenchloride; dmap; 2,6-dichloro-benzonitrile; In 1,4-dioxane; methanol; water; ethyl acetate; toluene; benzene;

DOI:10.1016/0040-4039(94)02196-I

Reference yield:

(3R,4S,5R)-4-Allyloxy-5-methyl-tetrahydro-furan-2,3-diol → (E)-(4S,7R)-7-Hydroxy-4-(4-methoxy-benzyloxy)-oct-2-enoic acid (E)-(1R,2S)-2-allyloxy-4-carboxy-1-methyl-but-3-enyl ester (161200-14-2)

Guidance literature:

Multi-step reaction with 6 steps

1: NaIO₄ / methanol

2: benzene / 80 °C

3: 92 percent / 2 percent HCl / dioxane; H₂O

4: DMAP / toluene / Ambient temperature

5: conc. HCl / methanol; ethyl acetate

6: DBN / benzene / Ambient temperature

With hydrogenchloride; dmap; sodium periodate; 2,6-dichloro-benzonitrile; In 1,4-dioxane; methanol; water; ethyl acetate; toluene; benzene;

DOI:10.1016/0040-4039(94)02196-I

upstream raw materials:

(E)-(4S,7R)-7-Hydroxy-4-(4-methoxy-benzyloxy)-oct-2-enoic acid (E)-(1R,2S)-2-allyloxy-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester

Formic acid (1R,2R)-2-allyloxy-1-methyl-3-oxo-propyl ester

(3aR,5R,6R,6aR)-6-Allyloxy-2,2,5-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

(E)-(4S,5R)-4-Allyloxy-5-hydroxy-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester

Downstream raw materials:

(3E,9E)-(5S,6R,11R,14R)-5,11-Dihydroxy-6,14-dimethyl-1,7-dioxa-cyclotetradeca-3,9-diene-2,8-dione

(3E,9E)-(5S,6R,11S,14R)-5-Allyloxy-11-(4-methoxy-benzyloxy)-6,14-dimethyl-1,7-dioxa-cyclotetradeca-3,9-diene-2,8-dione