5-(N-benzylamino)-6,7-O-isopropylidene-8-O-benzyl-2,3,5-trideoxy-L-talo-oct-2-enono-1,4-lactone

Base Information

• Chemical Name: 5-(N-benzylamino)-6,7-O-isopropylidene-8-O-benzyl-2,3,5-trideoxy-L-talo-oct-2-enono-1,4-lactone
• CAS No.: 148216-37-9
• Molecular Formula: C₂₅H₂₉NO₅
• Molecular Weight: 423.509

Synonyms:5-(N-benzylamino)-6,7-O-isopropylidene-8-O-benzyl-2,3,5-trideoxy-L-talo-oct-2-enono-1,4-lactone

Chemical Property of 5-(N-benzylamino)-6,7-O-isopropylidene-8-O-benzyl-2,3,5-trideoxy-L-talo-oct-2-enono-1,4-lactone

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Technology Process of 5-(N-benzylamino)-6,7-O-isopropylidene-8-O-benzyl-2,3,5-trideoxy-L-talo-oct-2-enono-1,4-lactone

There total 3 articles about 5-(N-benzylamino)-6,7-O-isopropylidene-8-O-benzyl-2,3,5-trideoxy-L-talo-oct-2-enono-1,4-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: 77.0%

2-(trimethylsiloxy)furan (65769-92-8) + 2,3-O-isopropylidene-4-O-benzyl-L-threose N-benzylimine (148261-02-3) → 5-(N-benzylamino)-6,7-O-isopropylidene-8-O-benzyl-2,3,5-trideoxy-L-talo-oct-2-enono-1,4-lactone (148216-37-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -85 ℃; for 4h;

DOI:10.1021/jo00064a031

Reference yield:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) → 5-(N-benzylamino)-6,7-O-isopropylidene-8-O-benzyl-2,3,5-trideoxy-L-talo-oct-2-enono-1,4-lactone (148216-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: MgSO₄ / diethyl ether / 2 h / Ambient temperature

2: 77 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / -85 °C

With boron trifluoride diethyl etherate; magnesium sulfate; In diethyl ether; dichloromethane;

DOI:10.1021/jo00064a031

Reference yield:

benzylamine (100-46-9) → 5-(N-benzylamino)-6,7-O-isopropylidene-8-O-benzyl-2,3,5-trideoxy-L-talo-oct-2-enono-1,4-lactone (148216-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: MgSO₄ / diethyl ether / 2 h / Ambient temperature

2: 77 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / -85 °C

With boron trifluoride diethyl etherate; magnesium sulfate; In diethyl ether; dichloromethane;

DOI:10.1021/jo00064a031

upstream raw materials:

2-(trimethylsiloxy)furan

2,3-O-isopropylidene-4-O-benzyl-L-threose N-benzylimine

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

benzylamine

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