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

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Chemical Name:benzyl 2,3-di-O-acetyl-4-O-(2'-nitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside
CAS No.:461026-23-3
Molecular Formula:C₃₁H₃₃NO₁₁
Molecular Weight:595.603
Hs Code.:

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

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

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

There total 9 articles about benzyl 2,3-di-O-acetyl-4-O-(2'-nitrophenyl)-6-O-para-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: 37.0%

: 824-38-4
potassium 2-nitrophenoxide

: 461026-22-2
benzyl 2,3-di-O-acetyl-6-O-para-methoxybenzyl-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside

: 461026-23-3
benzyl 2,3-di-O-acetyl-4-O-(2'-nitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: In N,N-dimethyl-formamide; at 80 ℃; for 2.5h;
DOI:10.1021/ja020627c

Reference yield:

: 10343-13-2,30657-70-6,31281-76-2,53729-76-3,142696-63-7,83113-54-6
benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

: 461026-23-3
benzyl 2,3-di-O-acetyl-4-O-(2'-nitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: NaOMe; MeOH / 20 °C

2: p-TsOH / dimethylformamide / 50 °C

3: pyridine / 20 °C

4: NaCNBH₃; TFA / tetrahydrofuran; CH₂Cl₂ / 19 h / 20 °C

5: pyridine / CH₂Cl₂ / -20 - 20 °C

6: 37 percent / dimethylformamide / 2.5 h / 80 °C

With pyridine; methanol; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Zemplen deacetylation;
DOI:10.1021/ja020627c

Reference yield:

: 25878-60-8
D-galactose pentaacetate

: 461026-23-3
benzyl 2,3-di-O-acetyl-4-O-(2'-nitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: HBr; AcOH / CH₂Cl₂ / 0 - 20 °C

2: 80 percent / Ag₂CO₃; I₂ / CH₂Cl₂ / 21 h

3: NaOMe; MeOH / 20 °C

4: p-TsOH / dimethylformamide / 50 °C

5: pyridine / 20 °C

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

7: pyridine / CH₂Cl₂ / -20 - 20 °C

8: 37 percent / dimethylformamide / 2.5 h / 80 °C

With pyridine; methanol; hydrogen bromide; iodine; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; silver carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: Koenigs-Knorr reaction / 3: Zemplen deacetylation;
DOI:10.1021/ja020627c