3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-allyl-N-benzylamino)-β-L-ido-hept-6-eno-1,4-furanose

Base Information

• Chemical Name: 3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-allyl-N-benzylamino)-β-L-ido-hept-6-eno-1,4-furanose
• CAS No.: 909705-91-5
• Molecular Formula: C₂₇H₃₃NO₄
• Molecular Weight: 435.563
• Mol file: 909705-91-5.mol

Synonyms:3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-allyl-N-benzylamino)-β-L-ido-hept-6-eno-1,4-furanose

Chemical Property of 3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-allyl-N-benzylamino)-β-L-ido-hept-6-eno-1,4-furanose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-allyl-N-benzylamino)-β-L-ido-hept-6-eno-1,4-furanose

There total 3 articles about 3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-allyl-N-benzylamino)-β-L-ido-hept-6-eno-1,4-furanose 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: 91.0%

allyl bromide (106-95-6) + 3-O-benzyl-5-deoxy-5-benzylamino-5-vinyl-1,2-O-isopropylidene-β-L-ido-1,4-pentofuranoside (299409-49-7) → 3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-allyl-N-benzylamino)-β-L-ido-hept-6-eno-1,4-furanose (909705-91-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/jo060823s

Reference yield:

C22H25NO5 → 3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-allyl-N-benzylamino)-β-L-ido-hept-6-eno-1,4-furanose (909705-91-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 11 percent / TMSOTf / tetrahydrofuran; diethyl ether / 1 h / -78 °C

2: 88 percent / zinc; acetic acid; Cu(OAc)2 / H₂O / 1 h / 80 °C

3: 91 percent / anhydrous potassium carbonate / dimethylformamide / 12 h / 20 °C

With copper diacetate; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; acetic acid; zinc; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1021/jo060823s

Reference yield:

N-benzyl-3-O-benzyl-5-deoxy-5-(hydroxylamino)-5-vinyl-1,2-O-isopropylidene-β-L-ido-1,4-pentofuranoside (299409-43-1) → 3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-allyl-N-benzylamino)-β-L-ido-hept-6-eno-1,4-furanose (909705-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / zinc; acetic acid; Cu(OAc)2 / H₂O / 1 h / 80 °C

2: 91 percent / anhydrous potassium carbonate / dimethylformamide / 12 h / 20 °C

With copper diacetate; potassium carbonate; acetic acid; zinc; In water; N,N-dimethyl-formamide;

DOI:10.1021/jo060823s

upstream raw materials:

allyl bromide

3-O-benzyl-5-deoxy-5-benzylamino-5-vinyl-1,2-O-isopropylidene-β-L-ido-1,4-pentofuranoside

N-benzyl-3-O-benzyl-5-deoxy-5-(hydroxylamino)-5-vinyl-1,2-O-isopropylidene-β-L-ido-1,4-pentofuranoside

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetra-deoxy-5,8-(N-benzylamino)-β-L-ido-octa-6-eno-1,4-furanose

5,8-dideoxy-5,8-(N-benzoxycarbonylimino)-1,2-O-isopropylidene-(6S,7R)-dihydroxy-α-D-erythro-L-ido-octa-1,4-furanose

5,8-dideoxy-5,8-(N-benzoxycarbonylimino)-1,2-O-isopropylidene-(6R,7S)-dihydroxy-α-L-erythro-L-ido-octa-1,4-furanose

3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-6(S),7(R)-di-hydroxy-α-D-erythro-L-ido-octa-1,4-furanose