3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-β-L-ido-7-eno-octo-1,4-furanose

Base Information

• Chemical Name: 3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-β-L-ido-7-eno-octo-1,4-furanose
• CAS No.: 690981-78-3
• Molecular Formula: C₂₅H₃₁NO₅
• Molecular Weight: 425.525
• Mol file: 690981-78-3.mol

Synonyms:3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-β-L-ido-7-eno-octo-1,4-furanose

Chemical Property of 3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-β-L-ido-7-eno-octo-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-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-β-L-ido-7-eno-octo-1,4-furanose

There total 1 articles about 3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-β-L-ido-7-eno-octo-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: 80.0%

(Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-ylidene)amine N-oxide (162740-21-8,191997-36-1) + allylmagnesium bromide (1730-25-2) → 3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-β-L-ido-7-eno-octo-1,4-furanose (690981-78-3) + 3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-α-D-gluco-7-eno-octo-1,4-furanose (690981-90-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1055/s-2004-829538

Reference yield: 92.0%

3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-β-L-ido-7-eno-octo-1,4-furanose (690981-78-3) → (S,E)-N-benzylidene-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine oxide (1384986-07-5)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 0 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tet.2012.05.126

Reference yield: 80.0%

3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-β-L-ido-7-eno-octo-1,4-furanose (690981-78-3) → (S)-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine (690981-80-7)

Guidance literature:

With copper diacetate; zinc; In acetic acid; at 70 ℃; for 1h;

DOI:10.1055/s-2004-829538

upstream raw materials:

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

allylmagnesium bromide

Downstream raw materials:

(S)-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine

1,2-O-isopropylidene-5,6,7,8,9-penta-deoxy-5,9-(N-benzoxycarbonyl-imino)-β-L-ido-nona-1,4-furanose

(S)-1-benzyl-2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-1,2,3,6-tetrahydropyridine

(S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine