phenyl 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside
CAS No.:246875-67-2
Molecular Formula:C₂₄H₂₇N₃O₇S
Molecular Weight:501.56
Hs Code.:

Synonyms:phenyl 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

There total 9 articles about phenyl 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-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:

: 246875-65-0
Acetic acid (2R,3R,4S,5S,6S)-2-acetoxymethyl-4-(4-methoxy-benzyloxy)-6-phenylsulfanyl-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

: 246875-67-2
phenyl 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 25 ℃;
DOI:10.1021/jo990811p

Reference yield:

: 77481-63-1
phenyl-1-thio-β-D-mannopyranoside

: 246875-67-2
phenyl 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 86 percent / pyridine / 24 h / 25 °C

2.1: 96 percent / CSA / acetone / 0.17 h / 25 °C

3.1: Bu₄NF / tetrahydrofuran / 24 h / 25 °C

4.1: pyridine / 2 h / 25 °C

5.1: 23.2 g / TFA / methanol / 2 h / 25 °C

6.1: Bu₂SnO / benzene / 2 h / Heating

6.2: 66 percent / Bu₄NI / benzene / 1.5 h / 65 - 70 °C

7.1: pyridine / CH₂Cl₂ / 0.33 h / -15 °C

8.1: 9.7 g / NaN₃ / dimethylformamide / 25 °C

With pyridine; sodium azide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 1.1: Silylation / 2.1: Etherification / 3.1: Desilylation / 4.1: Acetylation / 5.1: Hydrolysis / 6.1: Acetal formation / 6.2: Benzylation / 7.1: Substitution / 8.1: Substitution;
DOI:10.1021/jo990811p

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 246875-67-2
phenyl 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: Bu₂SnO / benzene / 2 h / Heating

1.2: 66 percent / Bu₄NI / benzene / 1.5 h / 65 - 70 °C

2.1: pyridine / CH₂Cl₂ / 0.33 h / -15 °C

3.1: 9.7 g / NaN₃ / dimethylformamide / 25 °C

With pyridine; sodium azide; di(n-butyl)tin oxide; In dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Acetal formation / 1.2: Benzylation / 2.1: Substitution / 3.1: Substitution;
DOI:10.1021/jo990811p