3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(N-benzyl-N-propenylamino)-α-D-gluco-7-eno-octo-1,4-furanose

Base Information

• Chemical Name: 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(N-benzyl-N-propenylamino)-α-D-gluco-7-eno-octo-1,4-furanose
• CAS No.: 760974-18-3
• Molecular Formula: C₂₈H₃₅NO₄
• Molecular Weight: 449.59
• Mol file: 760974-18-3.mol

Synonyms:3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(N-benzyl-N-propenylamino)-α-D-gluco-7-eno-octo-1,4-furanose

Chemical Property of 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(N-benzyl-N-propenylamino)-α-D-gluco-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-5,6-dideoxy-1,2-O-isopropylidene-5-(N-benzyl-N-propenylamino)-α-D-gluco-7-eno-octo-1,4-furanose

There total 2 articles about 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(N-benzyl-N-propenylamino)-α-D-gluco-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: 71.0%

allyl bromide (106-95-6) + 3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-N-(benzylamino)-α-D-gluco-7-eno-octo-1,4-furanose (690981-92-1) → 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(N-benzyl-N-propenylamino)-α-D-gluco-7-eno-octo-1,4-furanose (760974-18-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 18h;

DOI:10.1055/s-2004-829538

Reference yield:

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) → 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(N-benzyl-N-propenylamino)-α-D-gluco-7-eno-octo-1,4-furanose (760974-18-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Zn; Cu(OAc)2 / acetic acid / 1 h / 70 °C

2: 71 percent / K₂CO₃ / dimethylformamide / 18 h / 25 °C

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

DOI:10.1055/s-2004-829538

Reference yield:

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-(N-benzyl-N-propenylamino)-α-D-gluco-7-eno-octo-1,4-furanose (760974-18-3) → 1,2-O-isopropylidene-5,6,7,8,9-penta-deoxy-5,9-(N-benzoxycarbonyl-imino)-α-D-gluco-nona-1,4-furanose (690981-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / benzylidene-bis-tricyclohexylphosphine-dichlororuthenium / benzene / 18 h / Heating

2: H₂ / Pd/C / methanol / 12 h / 25 °C

3: NaHCO₃ / aq. ethanol / 2 h / 0 - 20 °C

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; Grubbs catalyst first generation; In methanol; ethanol; benzene;

DOI:10.1055/s-2004-829538

upstream raw materials:

allyl bromide

3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-N-(benzylamino)-α-D-gluco-7-eno-octo-1,4-furanose

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

Downstream raw materials:

1,2-O-isopropylidene-5,6,7,8,9-penta-deoxy-5,9-(N-benzoxycarbonyl-imino)-α-D-gluco-nona-1,4-furanose