ethyl (4S,5S,2E)-6-benzoyloxy-4,5-isopropylidenedioxyhex-2-enoate

Base Information

• Chemical Name: ethyl (4S,5S,2E)-6-benzoyloxy-4,5-isopropylidenedioxyhex-2-enoate
• CAS No.: 124575-37-7
• Molecular Formula: C₁₈H₂₂O₆
• Molecular Weight: 334.369
• Mol file: 124575-37-7.mol

Synonyms:ethyl (4S,5S,2E)-6-benzoyloxy-4,5-isopropylidenedioxyhex-2-enoate

Chemical Property of ethyl (4S,5S,2E)-6-benzoyloxy-4,5-isopropylidenedioxyhex-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (4S,5S,2E)-6-benzoyloxy-4,5-isopropylidenedioxyhex-2-enoate

There total 1 articles about ethyl (4S,5S,2E)-6-benzoyloxy-4,5-isopropylidenedioxyhex-2-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: 60.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (+)-(4R-trans)-5-<(benzoyloxy)methyl>-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde (77332-99-1) → ethyl (4S,5S,2E)-6-benzoyloxy-4,5-isopropylidenedioxyhex-2-enoate (124575-37-7)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; at 0 ℃; for 1.83333h;

DOI:10.1016/S0040-4020(01)83439-6

Reference yield: 79.0%

ethyl (4S,5S,2E)-6-benzoyloxy-4,5-isopropylidenedioxyhex-2-enoate (124575-37-7) → Benzoic acid (4S,5S)-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (124575-38-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)83439-6

Reference yield:

ethyl (4S,5S,2E)-6-benzoyloxy-4,5-isopropylidenedioxyhex-2-enoate (124575-37-7) → (S)-1-Benzoyl-3-{3-[(4S,5S)-5-((3E,5E,7E)-3,7-dimethyl-nona-3,5,7-trienyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propionyl}-5-isobutyl-pyrrolidin-2-one (124575-46-8,124602-07-9,124602-08-0,124602-09-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 79 percent / H₂ / Pd/C / ethanol / 2.5 h / Ambient temperature

2: 91 percent / Na / ethanol / 0.25 h

3: DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 0.75 h / -78 °C

4: 72 percent / benzene / 16 h / Heating

5: 88 percent / H₂ / Pd/C / ethyl acetate

7: 97 percent / NaOH / ethanol; H₂O / 1.5 h / Ambient temperature

8: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature

9: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C

With sodium hydroxide; oxalyl dichloride; hydrogen; sodium; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; ethyl acetate; benzene;

DOI:10.1016/S0040-4020(01)83439-6

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(+)-(4R-trans)-5-<(benzoyloxy)methyl>-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde

Downstream raw materials:

Benzoic acid (4S,5S)-5-(2-ethoxycarbonyl-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

isoaspochalasin C

(5S,4'S,5'S,8'EZ,10'E,12'E)-N-benzoyl-3-(8,12-dimethyl-4,5-isopropylidenedioxy-1-oxotetradeca-8,10,12-trienyl)-5-(2-methylpropyl)-Δ³-pyrrolin-2-one

(S)-1-Benzoyl-3-{3-[(4S,5S)-5-((3E,5E,7E)-3,7-dimethyl-nona-3,5,7-trienyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propionyl}-5-isobutyl-pyrrolidin-2-one