(2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate

Base Information

• Chemical Name: (2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate
• CAS No.: 737830-25-0
• Molecular Formula: C₂₆H₂₃NO₁₅
• Molecular Weight: 589.466
• Mol file: 737830-25-0.mol

Synonyms:(2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate

Chemical Property of (2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate

There total 7 articles about (2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate 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: 52.0%

di-tert-butyl (2S,3S)-3-benzyloxy-N-{[6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate (737830-24-9) → (2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate (737830-25-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2004.04.011

Reference yield:

di-tert-butyl (2S,3S)-3-benzyloxyaspartate (737830-18-1) → (2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate (737830-25-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 110.6 mg / i-Pr₂NEt / CH₂Cl₂ / 0.17 h

2: 52 percent / TFA / CH₂Cl₂ / 0 - 20 °C

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.bmc.2004.04.011

Reference yield:

di-tert-butyl (2S,3S)-3-benzyloxy-N-tert-butoxycarbonylaspartate → (2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate (737830-25-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / TFA / CH₂Cl₂ / 1 h / 0 °C

2: 110.6 mg / i-Pr₂NEt / CH₂Cl₂ / 0.17 h

3: 52 percent / TFA / CH₂Cl₂ / 0 - 20 °C

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.bmc.2004.04.011

upstream raw materials:

di-tert-butyl (2S,3S)-3-benzyloxy-N-{[6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate

di-tert-butyl (2S,3S)-3-benzyloxyaspartate

6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-carbaldehyde

6,7-bis(tert-butoxycarbonylmethoxy)-4-(hydroxymethoxy)coumarin