allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Base Information

• Chemical Name: allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
• CAS No.: 113599-90-9
• Molecular Formula: C₂₄H₂₅N₃O₈
• Molecular Weight: 483.478
• Mol file: 113599-90-9.mol

Synonyms:allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Chemical Property of allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

There total 4 articles about allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate 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: 81.0%

allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-<2-(phenylseleno)ethyl>-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-83-0) → allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-90-9)

Guidance literature:

With pyridine; dihydrogen peroxide; In dichloromethane; water; for 0.333333h;

DOI:10.1021/jm00401a020

Reference yield:

D-4-hydroxyphenylglycine (22818-40-2) → allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-90-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / 1N NaOH / diethyl ether; H₂O; dioxane / 1 h / ice bath

2: EEDQ / ethyl acetate / 3 h / Ambient temperature

3: 81 percent / pyridine, 30percent H₂O₂ / CH₂Cl₂; H₂O / 0.33 h

With pyridine; sodium hydroxide; dihydrogen peroxide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In 1,4-dioxane; diethyl ether; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm00401a020

Reference yield:

(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine (84792-41-6) → allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1: EEDQ / ethyl acetate / 3 h / Ambient temperature

2: 81 percent / pyridine, 30percent H₂O₂ / CH₂Cl₂; H₂O / 0.33 h

With pyridine; dihydrogen peroxide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; water; ethyl acetate;

DOI:10.1021/jm00401a020

upstream raw materials:

allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-<2-(phenylseleno)ethyl>-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

D-4-hydroxyphenylglycine

(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine

allyl (6S,7S)-7-amino-3-<2-(phenylseleno)ethyl>-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Downstream raw materials:

(6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid