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

Base Information

• Chemical Name: 3-O-benzyl-5-deoxy-5-benzylamino-5-vinyl-1,2-O-isopropylidene-β-L-ido-1,4-pentofuranoside
• CAS No.: 299409-49-7
• Molecular Formula: C₂₄H₂₉NO₄
• Molecular Weight: 395.499
• Mol file: 299409-49-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 3-O-benzyl-5-deoxy-5-benzylamino-5-vinyl-1,2-O-isopropylidene-β-L-ido-1,4-pentofuranoside 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: 88.0%

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-5-deoxy-5-benzylamino-5-vinyl-1,2-O-isopropylidene-β-L-ido-1,4-pentofuranoside (299409-49-7)

Guidance literature:

With copper diacetate; acetic acid; zinc; In water; at 80 ℃; for 1h;

DOI:10.1021/jo060823s

Reference yield:

(Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-ylidene)amine N-oxide (162740-21-8,191997-36-1) → 3-O-benzyl-5-deoxy-5-benzylamino-5-vinyl-1,2-O-isopropylidene-β-L-ido-1,4-pentofuranoside (299409-49-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 0 °C

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

With copper diacetate; zinc; In tetrahydrofuran; water; acetic acid;

DOI:10.1021/jo0601617

Reference yield:

C22H25NO5 → 3-O-benzyl-5-deoxy-5-benzylamino-5-vinyl-1,2-O-isopropylidene-β-L-ido-1,4-pentofuranoside (299409-49-7)

Guidance literature:

Multi-step reaction with 2 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

With copper diacetate; trimethylsilyl trifluoromethanesulfonate; acetic acid; zinc; In tetrahydrofuran; diethyl ether; water;

DOI:10.1021/jo060823s

upstream raw materials:

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

(Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-ylidene)amine N-oxide

Downstream raw materials:

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

3-O-benzyl-1,2-O-isopropylidene-5,8-dideoxy-5,8-(N-benzylamino)-(6R,7S)-di-hydroxy-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

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