(3R,4S,5R)-arabino-3-benzylamino-trideoxyaldonic acid δ-lactone

Base Information

• Chemical Name: (3R,4S,5R)-arabino-3-benzylamino-trideoxyaldonic acid δ-lactone
• CAS No.: 194229-43-1
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235.283
• Mol file: 194229-43-1.mol

Synonyms:(3R,4S,5R)-arabino-3-benzylamino-trideoxyaldonic acid δ-lactone

Chemical Property of (3R,4S,5R)-arabino-3-benzylamino-trideoxyaldonic acid δ-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-arabino-3-benzylamino-trideoxyaldonic acid δ-lactone

There total 4 articles about (3R,4S,5R)-arabino-3-benzylamino-trideoxyaldonic acid δ-lactone 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: 64.0%

methyl (3R,4S,5S)-3-benzylamino-4,5-epoxyhexanoate (194229-40-8) → (3R,4S,5R)-arabino-3-benzylamino-trideoxyaldonic acid δ-lactone (194229-43-1) + (3R,4S,5R)-arabino-3-benzylamino-trideoxyaldonic acid γ-lactone

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at -20 ℃;

Reference yield:

methyl (4S,5S)-(4,5)-epoxy-2(E)-hexenoate (67315-16-6) → (3R,4S,5R)-arabino-3-benzylamino-trideoxyaldonic acid δ-lactone (194229-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / 48 h / 40 °C

2: 64 percent / CF₃SO₃H / CH₂Cl₂ / 4 h / -20 °C

With trifluorormethanesulfonic acid; In dichloromethane; 1: Addition / 2: lactonization;

DOI:10.1016/S0957-4166(00)00395-5

Reference yield:

benzylamine (100-46-9) → (3R,4S,5R)-arabino-3-benzylamino-trideoxyaldonic acid δ-lactone (194229-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / 40 °C

2: 64 percent / CF₃SO₃H / CH₂Cl₂ / -20 °C

With trifluorormethanesulfonic acid; In dichloromethane;

upstream raw materials:

methyl (3R,4S,5S)-3-benzylamino-4,5-epoxyhexanoate

methyl (4S,5S)-(4,5)-epoxy-2(E)-hexenoate

benzylamine

Downstream raw materials:

N-benzoyl-α-D-acosamine