(Z),2(R),7(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-7,8-dihydroxy-oct-4-enoate

Base Information

• Chemical Name: (Z),2(R),7(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-7,8-dihydroxy-oct-4-enoate
• CAS No.: 192515-90-5
• Molecular Formula: C₁₈H₂₆O₆
• Molecular Weight: 338.401
• Mol file: 192515-90-5.mol

Synonyms:(Z),2(R),7(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-7,8-dihydroxy-oct-4-enoate

Chemical Property of (Z),2(R),7(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-7,8-dihydroxy-oct-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z),2(R),7(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-7,8-dihydroxy-oct-4-enoate

There total 4 articles about (Z),2(R),7(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-7,8-dihydroxy-oct-4-enoate 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:

(Z),2(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hex-4-enoate (192515-54-1) → (Z),2(R),7(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-7,8-dihydroxy-oct-4-enoate (192515-90-5)

Guidance literature:

With acetic acid; at 55 ℃; for 0.333333h;

DOI:10.1021/ja9709132

Reference yield:

(R)-3-Benzyloxymethoxy-dihydro-furan-2-one → (Z),2(R),7(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-7,8-dihydroxy-oct-4-enoate (192515-90-5)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃

3: 72 percent / tetrahydrofuran; hexane / 0.1 h / -78 - 20 °C

4: aq. acetic acid / 0.33 h / 55 °C

With potassium carbonate; acetic acid; In tetrahydrofuran; hexane; 1: ethanolysis / 2: Swern oxidation / 3: Wittig reaction / 4: Hydrolysis;

DOI:10.1021/ja9709132

Reference yield:

(R)-2-Benzyloxymethoxy-4-oxo-butyric acid ethyl ester (192515-53-0) → (Z),2(R),7(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-7,8-dihydroxy-oct-4-enoate (192515-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / tetrahydrofuran; hexane / 0.1 h / -78 - 20 °C

2: aq. acetic acid / 0.33 h / 55 °C

With acetic acid; In tetrahydrofuran; hexane; 1: Wittig reaction / 2: Hydrolysis;

DOI:10.1021/ja9709132

upstream raw materials:

(Z),2(R)-ethyl-2-[[(benzyloxy)methyl]oxy]-6-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hex-4-enoate

(R)-2-Benzyloxymethoxy-4-oxo-butyric acid ethyl ester

Downstream raw materials:

(Z),2(R),7(R)-2-[[(benzyloxy)methyl]oxy]-8-[(tert-butyldiphenylsilyl)oxy]-7-hydroxy-oct-4-enoic acid