benzyl 2,3-di-O-acetyl-4-O-(2',4'-dinitrophenyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

Base Information

Chemical Name:benzyl 2,3-di-O-acetyl-4-O-(2',4'-dinitrophenyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranoside
CAS No.:461026-15-3
Molecular Formula:C₃₁H₃₂N₂O₁₃
Molecular Weight:640.601
Hs Code.:

Synonyms:benzyl 2,3-di-O-acetyl-4-O-(2',4'-dinitrophenyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

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Chemical Property of benzyl 2,3-di-O-acetyl-4-O-(2',4'-dinitrophenyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

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Technology Process of benzyl 2,3-di-O-acetyl-4-O-(2',4'-dinitrophenyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

There total 8 articles about benzyl 2,3-di-O-acetyl-4-O-(2',4'-dinitrophenyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranoside 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%

: 70-34-8,65727-75-5
2,4-Dinitrofluorobenzene

: 461026-03-9
benzyl 2,3-di-O-acetyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

: 461026-15-3
benzyl 2,3-di-O-acetyl-4-O-(2',4'-dinitrophenyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

Guidance literature:: With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1021/ja020627c

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-glucose pentaacetate

: 461026-15-3
benzyl 2,3-di-O-acetyl-4-O-(2',4'-dinitrophenyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / HBr; AcOH / CH₂Cl₂ / 0 - 20 °C

2: 68 percent / Ag₂CO₃; I₂ / CH₂Cl₂ / 15 h / 20 °C

3: 99 percent / NaOMe; MeOH / 20 °C

4: 63 percent / camphorsulfonic acid / CHCl₃ / 2 h / Heating

5: 90 percent / pyridine / 20 °C

6: 91 percent / NaCNBH₃; TFA / tetrahydrofuran; CH₂Cl₂ / 19 h / 20 °C

7: 80 percent / DABCO / dimethylformamide / 24 h / 20 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; methanol; camphor-10-sulfonic acid; hydrogen bromide; iodine; sodium methylate; sodium cyanoborohydride; acetic acid; silver carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; 2: Koenigs-Knorr reaction / 3: Zemplen deacetylation;
DOI:10.1021/ja020627c

Reference yield:

: 4304-12-5
(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

: 461026-15-3
benzyl 2,3-di-O-acetyl-4-O-(2',4'-dinitrophenyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 63 percent / camphorsulfonic acid / CHCl₃ / 2 h / Heating

2: 90 percent / pyridine / 20 °C

3: 91 percent / NaCNBH₃; TFA / tetrahydrofuran; CH₂Cl₂ / 19 h / 20 °C

4: 80 percent / DABCO / dimethylformamide / 24 h / 20 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; camphor-10-sulfonic acid; sodium cyanoborohydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/ja020627c