(E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl ester
• CAS No.: 162210-51-7
• Molecular Formula: C₂₉H₄₆O₇
• Molecular Weight: 506.68
• Mol file: 162210-51-7.mol

Synonyms:(E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl ester

Chemical Property of (E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl ester

There total 16 articles about (E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl 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: 93.0%

Triethyl orthoacetate (78-39-7) + (Z)-(2R,3S,4S,7R)-3-Benzyloxy-8-(2-isobutyl-[1,3]dioxolan-2-yl)-2-methoxymethoxy-7-methyl-oct-5-en-4-ol (162210-50-6) → (E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl ester (162210-51-7)

Guidance literature:

propionic acid; at 120 ℃; for 4h;

DOI:10.1016/0040-4039(94)80021-9

Reference yield:

(R)-1-Iodo-2,6-dimethyl-heptan-4-one (162210-61-9) → (E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl ester (162210-51-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / toluene / 10 h / 110 °C

2: 82 percent / PTSA / benzene / 48 h / 80 °C

3: 62 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C, 3 h, room t., 1 h

4: 95 percent / K₂CO₃ / methanol / 5 h / 40 °C

5: 93 percent / EtCOOH / 4 h / 120 °C

With n-butyllithium; potassium carbonate; toluene-4-sulfonic acid; propionic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; toluene; benzene;

DOI:10.1016/0040-4039(94)80021-9

Reference yield:

2-(2-Ethoxy-ethoxy)-4-methyl-pentanenitrile → (E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl ester (162210-51-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / LDA / hexamethylphosphoric acid triamide; tetrahydrofuran / 1.) -78 deg C, 2 h to room t., 3 h

2: 85 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

3: pyridine / CHCl₃ / 8 h / Ambient temperature

4: NaI / butan-2-one / 3 h / 80 °C

5: 5percent H₂SO₄ / methanol / 0.5 h / Ambient temperature

6: 0.5N NaOH / diethyl ether / 0.17 h

7: 88 percent / toluene / 10 h / 110 °C

8: 82 percent / PTSA / benzene / 48 h / 80 °C

9: 62 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C, 3 h, room t., 1 h

10: 95 percent / K₂CO₃ / methanol / 5 h / 40 °C

11: 93 percent / EtCOOH / 4 h / 120 °C

With pyridine; sodium hydroxide; n-butyllithium; sulfuric acid; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; sodium iodide; lithium diisopropyl amide; propionic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; chloroform; toluene; butanone; benzene;

DOI:10.1016/0040-4039(94)80021-9

upstream raw materials:

Triethyl orthoacetate

(Z)-(2R,3S,4S,7R)-3-Benzyloxy-8-(2-isobutyl-[1,3]dioxolan-2-yl)-2-methoxymethoxy-7-methyl-oct-5-en-4-ol

(R)-1-Iodo-2,6-dimethyl-heptan-4-one

Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester

Downstream raw materials:

(-)-Reiswigin A