3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-D-glucitol

Base Information

Chemical Name:3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-D-glucitol
CAS No.:639808-07-4
Molecular Formula:C₂₅H₃₃N₃O₄Si
Molecular Weight:467.64
Hs Code.:

Synonyms:3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-D-glucitol

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Chemical Property of 3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-D-glucitol

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Technology Process of 3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-D-glucitol

There total 7 articles about 3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-D-glucitol 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: 99.0%

: 639808-06-3
3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol

: 639808-07-4
3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-D-glucitol

Guidance literature:: With chlorotriisopropylsilane; trifluoroacetic acid; In dichloromethane; for 0.5h;
DOI:10.1021/jo0349429

Reference yield:

: 106248-72-0
2,5-Anhydro-1,3-O-isopropyliden-6-O-(p-tosyl)-D-glucitol

: 639808-07-4
3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-D-glucitol

Guidance literature:: Multi-step reaction with 6 steps

1: sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 16 h / 80 °C

2: 33 g / imidazole / dimethylformamide / 20 °C

3: trifluoroacetic acid / methanol; CH₂Cl₂ / 3 h

4: pyridine / 16 h

5: 7.8 g / potassium hexamethyldisilazane (KHMDS) / dimethylformamide; toluene / 0 - 20 °C

6: 99 percent / triisopropylsilane (TiPSH); TFA / CH₂Cl₂ / 0.5 h

With pyridine; 1H-imidazole; sodium azide; potassium hexamethyldisilazane; chlorotriisopropylsilane; tetra-(n-butyl)ammonium iodide; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0349429

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 639808-07-4
3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-D-glucitol

Guidance literature:: Multi-step reaction with 5 steps

1: 33 g / imidazole / dimethylformamide / 20 °C

2: trifluoroacetic acid / methanol; CH₂Cl₂ / 3 h

3: pyridine / 16 h

4: 7.8 g / potassium hexamethyldisilazane (KHMDS) / dimethylformamide; toluene / 0 - 20 °C

5: 99 percent / triisopropylsilane (TiPSH); TFA / CH₂Cl₂ / 0.5 h

With pyridine; 1H-imidazole; potassium hexamethyldisilazane; chlorotriisopropylsilane; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0349429