(E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside

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Chemical Name:(E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside
CAS No.:351030-64-3
Molecular Formula:C₄₁H₄₉N₃O₆Si
Molecular Weight:707.942
Hs Code.:

Synonyms:(E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside

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Chemical Property of (E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside

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Technology Process of (E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside

There total 7 articles about (E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-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: 78.0%

: 351030-62-1
(R/S)-But-3-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside

: 351030-64-3
(E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: With n-butyllithium; Wilkinson's catalyst; In tetrahydrofuran; at 1 ℃; Heating;
DOI:10.1039/b009845k

Reference yield:

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

: 351030-64-3
(E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; n-butyllithium; sodium hydride; toluene-4-sulfonic acid; acetic acid; Wilkinson's catalyst; In tetrahydrofuran; 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

: 351030-64-3
(E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; methanol; n-butyllithium; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; Wilkinson's catalyst; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;
DOI:10.1039/b009845k