(R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

Base Information

Chemical Name:(R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside
CAS No.:351030-74-5
Molecular Formula:C₆₀H₆₇N₃O₁₁Si
Molecular Weight:1034.29
Hs Code.:

Synonyms:(R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

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Chemical Property of (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

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Technology Process of (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

There total 17 articles about (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-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: 99.5%

: 351030-72-3
(R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

: 351030-74-5
(R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 1.5h;
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

: 351030-74-5
(R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

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: 30 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂; diethyl ether / 0.5 h / -20 °C

9.1: 99.5 percent / aq. TFA / CH₂Cl₂ / 1.5 h

With 1H-imidazole; methanol; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; Wilkinson's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/b009845k

Reference yield:

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

: 351030-74-5
(R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

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: 30 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂; diethyl ether / 0.5 h / -20 °C

8.1: 99.5 percent / aq. TFA / CH₂Cl₂ / 1.5 h

With 1H-imidazole; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; Wilkinson's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/b009845k