phenyl 6-azido-6-deoxy-3,4-di-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside

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Chemical Name:phenyl 6-azido-6-deoxy-3,4-di-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside
CAS No.:760966-16-3
Molecular Formula:C₃₅H₄₇N₃O₅Si
Molecular Weight:617.861
Hs Code.:

Synonyms:phenyl 6-azido-6-deoxy-3,4-di-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside

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Chemical Property of phenyl 6-azido-6-deoxy-3,4-di-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside

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Technology Process of phenyl 6-azido-6-deoxy-3,4-di-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside

There total 6 articles about phenyl 6-azido-6-deoxy-3,4-di-O-benzyl-2-O-triisopropylsilyl-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: 81.0%

: 100-39-0
benzyl bromide

: 760966-09-4
phenyl 6-azido-6-deoxy-3-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside

: 760966-16-3
phenyl 6-azido-6-deoxy-3,4-di-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;
DOI:10.1016/j.tet.2004.05.080

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 760966-16-3
phenyl 6-azido-6-deoxy-3,4-di-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2.1: TFA / CH₂Cl₂ / 6 h

3.1: 7.86 g / pyridine / CH₂Cl₂ / 16 h

4.1: Na; amberlite IR-120 (plus) / methanol / 0.08 h

4.2: 85 percent / pyridine / 3 h / 0 °C

5.1: 72 percent / NAN₃ / dimethylformamide / 16 h / 90 °C

6.1: 81 percent / NaH / dimethylformamide / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium azide; Amberlite IR-120 (plus); sodium; sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.05.080

Reference yield:

: 103082-82-2
phenyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

: 760966-16-3
phenyl 6-azido-6-deoxy-3,4-di-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2.1: TFA / CH₂Cl₂ / 6 h

3.1: 7.86 g / pyridine / CH₂Cl₂ / 16 h

4.1: Na; amberlite IR-120 (plus) / methanol / 0.08 h

4.2: 85 percent / pyridine / 3 h / 0 °C

5.1: 72 percent / NAN₃ / dimethylformamide / 16 h / 90 °C

6.1: 81 percent / NaH / dimethylformamide / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium azide; Amberlite IR-120 (plus); sodium; sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.05.080