tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside
CAS No.:506441-97-0
Molecular Formula:C₃₂H₅₃NO₉Si
Molecular Weight:623.86
Hs Code.:

Synonyms:tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

There total 11 articles about tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-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: 59.0%

: 506441-95-8
1,6-di-tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

: 506441-97-0
tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

Guidance literature:: With hydrogen fluoride; In acetonitrile; for 0.5h;
DOI:10.1021/ja0284456

Reference yield:

: 2051-49-2
n-hexanoic anhydride

: 506441-97-0
tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / 8 h

2: 5.13 g / PPTS; MeOH / 3 h / Heating

3: 91 percent / imidazole / acetonitrile / 4 h

4: 71 percent / DMAP / CH₂Cl₂ / 16 h / 20 °C

5: 59 percent / aq. HF / acetonitrile / 0.5 h

With pyridine; 1H-imidazole; methanol; dmap; hydrogen fluoride; pyridinium p-toluenesulfonate; In dichloromethane; acetonitrile;
DOI:10.1021/ja0284456

Reference yield:

: 13996-79-7
2-Desoxy-2-hexanoylamino-D-glucose

: 506441-97-0
tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: pyridine / CH₂Cl₂ / 6 h / Heating

2: 10.4 g / ethylenediamine; AcOH / tetrahydrofuran / 2 h

3: imidazole / acetonitrile / 4 h

4: NH₃ / methanol / 8 h / 0 °C

5: 6.97 g / PPTS / CH₂Cl₂ / 4 h / Heating

6: pyridine / CH₂Cl₂ / 8 h

7: 5.13 g / PPTS; MeOH / 3 h / Heating

8: 91 percent / imidazole / acetonitrile / 4 h

9: 71 percent / DMAP / CH₂Cl₂ / 16 h / 20 °C

10: 59 percent / aq. HF / acetonitrile / 0.5 h

With pyridine; 1H-imidazole; methanol; dmap; hydrogen fluoride; ammonia; pyridinium p-toluenesulfonate; acetic acid; ethylenediamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/ja0284456