2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride

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Chemical Name:2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride
CAS No.:351030-70-1
Molecular Formula:C₃₇H₄₂FN₃O₅Si
Molecular Weight:655.841
Hs Code.:

Synonyms:2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride

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Chemical Property of 2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride

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Technology Process of 2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride

There total 9 articles about 2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride 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%

: (3R,4R,5S,6R)-3-Azido-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ol

: 351030-70-1
2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride

Guidance literature:: With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at -30 ℃; for 0.333333h;
DOI:10.1039/b009845k

Reference yield:

: (2R,3S,4R,5R,6R)-5-Azido-2-hydroxymethyl-6-(1-methyl-allyloxy)-tetrahydro-pyran-3,4-diol

: 351030-70-1
2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride

Guidance literature:: Multi-step reaction with 8 steps

1.1: 3.6 g / p-TsOH / acetone / 5 h / 40 °C / pH 4

2.1: NaH / dimethylformamide / 2 h / 20 °C

3.1: aq. AcOH / 8 h / 50 °C

4.1: 3.8 g / imidazole / dimethylformamide / 18 h / 20 °C

5.1: NaH / dimethylformamide

5.2: 70.2 percent / dimethylformamide / 5 h / 20 °C

6.1: 78 percent / BuLi / Wilkinson's catalyst / tetrahydrofuran / 1 °C / Heating

7.1: H₂O; HgO; HgBr₂ / acetone / 18 h

8.1: 80 percent / DAST / CH₂Cl₂ / 0.33 h / -30 °C

With 1H-imidazole; n-butyllithium; water; sodium hydride; toluene-4-sulfonic acid; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; mercury dibromide; mercury(II) oxide; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/b009845k

Reference yield:

: 312612-85-4
(R/S)-3-buten-2-yl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside

: 351030-70-1
2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaOMe; MeOH / 3 h

2.1: 3.6 g / p-TsOH / acetone / 5 h / 40 °C / pH 4

3.1: NaH / dimethylformamide / 2 h / 20 °C

4.1: aq. AcOH / 8 h / 50 °C

5.1: 3.8 g / imidazole / dimethylformamide / 18 h / 20 °C

6.1: NaH / dimethylformamide

6.2: 70.2 percent / dimethylformamide / 5 h / 20 °C

7.1: 78 percent / BuLi / Wilkinson's catalyst / tetrahydrofuran / 1 °C / Heating

8.1: H₂O; HgO; HgBr₂ / acetone / 18 h

9.1: 80 percent / DAST / CH₂Cl₂ / 0.33 h / -30 °C

With 1H-imidazole; methanol; n-butyllithium; water; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; mercury dibromide; mercury(II) oxide; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/b009845k