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

Base Information

• Chemical Name: 3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-benzyl-N-benzoxycarbonylamino)-β-L-ido-6-eno-hepta-1,4-furanose
• CAS No.: 899431-76-6
• Molecular Formula: C₃₂H₃₅NO₆
• Molecular Weight: 529.633
• Mol file: 899431-76-6.mol

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

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

There total 3 articles about 3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-benzyl-N-benzoxycarbonylamino)-β-L-ido-6-eno-hepta-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: 90.0%

benzyl chloroformate (501-53-1,94274-21-2) + 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-benzyl-N-benzoxycarbonylamino)-β-L-ido-6-eno-hepta-1,4-furanose (899431-76-6)

Guidance literature:

With sodium hydrogencarbonate; In methanol; water; at 0 ℃; for 3h;

DOI:10.1021/jo0601617

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-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-benzyl-N-benzoxycarbonylamino)-β-L-ido-6-eno-hepta-1,4-furanose (899431-76-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 0 °C

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

3: 90 percent / sodium bicarbonate / methanol; H₂O / 3 h / 0 °C

With copper diacetate; sodium hydrogencarbonate; zinc; In tetrahydrofuran; methanol; water; acetic acid;

DOI:10.1021/jo0601617

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-benzyl-N-benzoxycarbonylamino)-β-L-ido-6-eno-hepta-1,4-furanose (899431-76-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 90 percent / sodium bicarbonate / methanol; H₂O / 3 h / 0 °C

With copper diacetate; sodium hydrogencarbonate; zinc; In methanol; water; acetic acid;

DOI:10.1021/jo0601617

upstream raw materials:

benzyl chloroformate

3-O-benzyl-5-deoxy-5-benzylamino-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

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

Downstream raw materials:

6-aldehydo-5-(N-benzyl-N-benzoxycarbonyl)amino-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-ido-hexo-1,4-furanose

(4S,5S)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-oxazolidin-2-one

(2S,3S)-1-Benzyl-2-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidin-3-ol

(1S,2S)-1-Benzylamino-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-en-2-ol