N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside

Base Information

• Chemical Name: N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside
• CAS No.: 147455-49-0
• Molecular Formula: C₂₂H₂₈N₂O₆S
• Molecular Weight: 448.54
• Mol file: 147455-49-0.mol

Synonyms:N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside

Chemical Property of N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside

There total 1 articles about N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside 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: 82.0%

2-bromo-1,3-thiazole (3034-53-5,215777-74-5) + (Z)-N-benzyl-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-ylidene)amine N-oxide (191997-37-2,147455-48-9) → N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-α-D-glycero-D-galacto-1,5-hexopyranoside (147455-50-3) + N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside (147455-49-0)

Guidance literature:

With diethylaluminium chloride; In diethyl ether; hexane; Yields of byproduct given; 1.) -78 deg C, 15 min, 2.) -80 deg C, 30 min;

Reference yield:

N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside (147455-49-0) → 1,2:3,4-di-O-isopropylidene-6--6-deoxy-L-glycero-α-D-galacto-heptopyranose (76951-87-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 20percent aq. TiCl₃ / methanol / 0.25 h / Ambient temperature

2: 7percent aq. NaHCO₃ / dioxane / 0.33 h / 0 °C

4: 98 percent / NaBH₄ / methanol / 1 h / 0 °C

With sodium tetrahydroborate; titanium(III) chloride; sodium hydrogencarbonate; In 1,4-dioxane; methanol;

Reference yield:

N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside (147455-49-0) → 6-(Benzyloxycarbonylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-D-galacto-heptodialdo-1,5-pyranose (147455-56-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 20percent aq. TiCl₃ / methanol / 0.25 h / Ambient temperature

2: 7percent aq. NaHCO₃ / dioxane / 0.33 h / 0 °C

With titanium(III) chloride; sodium hydrogencarbonate; In 1,4-dioxane; methanol;

upstream raw materials:

2-bromo-1,3-thiazole

(Z)-N-benzyl-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-ylidene)amine N-oxide

Downstream raw materials:

1,2:3,4-di-O-isopropylidene-6--6-deoxy-L-glycero-α-D-galacto-heptopyranose

6-(Benzyloxycarbonylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-D-galacto-heptodialdo-1,5-pyranose

6-(Benzyloxycarbonylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside