2,4-dinitrophenyl 4,8-anhydro-7-deoxy-2,3,6-tri-O-methyl-α-L-glycero-D-glucooctopyranoside

Base Information

• Chemical Name: 2,4-dinitrophenyl 4,8-anhydro-7-deoxy-2,3,6-tri-O-methyl-α-L-glycero-D-glucooctopyranoside
• CAS No.: 753491-03-1
• Molecular Formula: C₁₇H₂₂N₂O₁₀
• Molecular Weight: 414.369

Synonyms:2,4-dinitrophenyl 4,8-anhydro-7-deoxy-2,3,6-tri-O-methyl-α-L-glycero-D-glucooctopyranoside

Chemical Property of 2,4-dinitrophenyl 4,8-anhydro-7-deoxy-2,3,6-tri-O-methyl-α-L-glycero-D-glucooctopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-dinitrophenyl 4,8-anhydro-7-deoxy-2,3,6-tri-O-methyl-α-L-glycero-D-glucooctopyranoside

There total 12 articles about 2,4-dinitrophenyl 4,8-anhydro-7-deoxy-2,3,6-tri-O-methyl-α-L-glycero-D-glucooctopyranoside 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:

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside (3013-58-9,3051-89-6,4261-46-5,6748-99-8,13035-20-6,13502-46-0,22893-88-5,35311-32-1,53767-28-5,56586-53-9,56586-54-0,69744-11-2,94480-09-8,120200-48-8,120200-49-9,120200-50-2,120200-52-4) → 2,4-dinitrophenyl 4,8-anhydro-7-deoxy-2,3,6-tri-O-methyl-α-L-glycero-D-glucooctopyranoside (753491-03-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / BH₃*THF; Sc(OTf)3 / CH₂Cl₂ / 6 h

2: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

3: TiCl₄ / CH₂Cl₂ / 2.5 h / -78 °C

4: NaH / dimethylformamide / 0.75 h / 20 °C

5: ozone / methanol; CH₂Cl₂ / -78 °C

6: NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

7: 901 mg / pyridine / 1.5 h

8: H₂; aq. HCl / Pd/C / methanol; ethyl acetate / 2 h / 760 Torr

9: 170 mg / NaH; NaI / dimethylformamide / 1 h / 20 °C

10: aq. HClO₄ / 0.25 h / 20 °C

11: MeONa / methanol

12: 210 mg / DABCO / dimethylformamide / 5 h / 20 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium tetrahydroborate; perchloric acid; borane-THF; hydrogen; sodium methylate; titanium tetrachloride; sodium hydride; Dess-Martin periodane; ozone; sodium iodide; scandium tris(trifluoromethanesulfonate); palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2: Dess-Martin oxidation / 3: Sakurai alkylation / 11: Zemplen deacetylation;

DOI:10.1021/ja047578j

Reference yield:

(2S,3S,4S,5R,6S)-3-Benzyloxy-4,5,6-trimethoxy-tetrahydro-pyran-2-carbaldehyde → 2,4-dinitrophenyl 4,8-anhydro-7-deoxy-2,3,6-tri-O-methyl-α-L-glycero-D-glucooctopyranoside (753491-03-1)

Guidance literature:

Multi-step reaction with 10 steps

1: TiCl₄ / CH₂Cl₂ / 2.5 h / -78 °C

2: NaH / dimethylformamide / 0.75 h / 20 °C

3: ozone / methanol; CH₂Cl₂ / -78 °C

4: NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

5: 901 mg / pyridine / 1.5 h

6: H₂; aq. HCl / Pd/C / methanol; ethyl acetate / 2 h / 760 Torr

7: 170 mg / NaH; NaI / dimethylformamide / 1 h / 20 °C

8: aq. HClO₄ / 0.25 h / 20 °C

9: MeONa / methanol

10: 210 mg / DABCO / dimethylformamide / 5 h / 20 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium tetrahydroborate; perchloric acid; hydrogen; sodium methylate; titanium tetrachloride; sodium hydride; ozone; sodium iodide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Sakurai alkylation / 9: Zemplen deacetylation;

DOI:10.1021/ja047578j

Reference yield:

methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside (83075-53-0,89177-22-0,129454-52-0,51433-19-3) → 2,4-dinitrophenyl 4,8-anhydro-7-deoxy-2,3,6-tri-O-methyl-α-L-glycero-D-glucooctopyranoside (753491-03-1)

Guidance literature:

Multi-step reaction with 11 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

2: TiCl₄ / CH₂Cl₂ / 2.5 h / -78 °C

3: NaH / dimethylformamide / 0.75 h / 20 °C

4: ozone / methanol; CH₂Cl₂ / -78 °C

5: NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

6: 901 mg / pyridine / 1.5 h

7: H₂; aq. HCl / Pd/C / methanol; ethyl acetate / 2 h / 760 Torr

8: 170 mg / NaH; NaI / dimethylformamide / 1 h / 20 °C

9: aq. HClO₄ / 0.25 h / 20 °C

10: MeONa / methanol

11: 210 mg / DABCO / dimethylformamide / 5 h / 20 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium tetrahydroborate; perchloric acid; hydrogen; sodium methylate; titanium tetrachloride; sodium hydride; Dess-Martin periodane; ozone; sodium iodide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Dess-Martin oxidation / 2: Sakurai alkylation / 10: Zemplen deacetylation;

DOI:10.1021/ja047578j

upstream raw materials:

2,4-Dinitrofluorobenzene

methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside

methyl 4,8-anhydro-7-deoxy-2,3,6-tri-O-methyl-β-L-glycero-D-gluco-octopyranoside

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