(2E,4S,5S)-2-methyl-4,5-isopropylidenedioxy-6-benzyloxy-2-hexenoic acid ethyl ester

Base Information

• Chemical Name: (2E,4S,5S)-2-methyl-4,5-isopropylidenedioxy-6-benzyloxy-2-hexenoic acid ethyl ester
• CAS No.: 320343-41-7
• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.412

Synonyms:(2E,4S,5S)-2-methyl-4,5-isopropylidenedioxy-6-benzyloxy-2-hexenoic acid ethyl ester

Chemical Property of (2E,4S,5S)-2-methyl-4,5-isopropylidenedioxy-6-benzyloxy-2-hexenoic acid ethyl ester

Chemical Property:

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Technology Process of (2E,4S,5S)-2-methyl-4,5-isopropylidenedioxy-6-benzyloxy-2-hexenoic acid ethyl ester

There total 2 articles about (2E,4S,5S)-2-methyl-4,5-isopropylidenedioxy-6-benzyloxy-2-hexenoic 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:

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (78469-77-9,81076-11-1,128820-40-6,78513-03-8) → (2E,4S,5S)-2-methyl-4,5-isopropylidenedioxy-6-benzyloxy-2-hexenoic acid ethyl ester (320343-41-7)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

2: 1.12 g / CH₂Cl₂ / 0.5 h / 0 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1: Swern oxidation / 2: Wittig reaction;

DOI:10.1021/jo005612g

Reference yield:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → (2E,4S,5S)-2-methyl-4,5-isopropylidenedioxy-6-benzyloxy-2-hexenoic acid ethyl ester (320343-41-7)

Guidance literature:

In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/jo005612g

Reference yield: 90.0%

(2E,4S,5S)-2-methyl-4,5-isopropylidenedioxy-6-benzyloxy-2-hexenoic acid ethyl ester (320343-41-7) → (2E,4S,5S)-1-hydroxy-2-methyl-4,5-O-isopropylidene-6-(benzyloxy)hex-2-ene-4,5-diol (320343-42-8)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 2.5h;

DOI:10.1021/jo005612g

upstream raw materials:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

(carbethoxyethylidene)triphenylphosphorane

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

Downstream raw materials:

(2E,4S,5S)-1-hydroxy-2-methyl-4,5-O-isopropylidene-6-(benzyloxy)hex-2-ene-4,5-diol

sphingofungin F

(2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol

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