tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

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Chemical Name:tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside
CAS No.:506442-03-1
Molecular Formula:C₇₂H₁₀₃N₂O₂₀PSi
Molecular Weight:1375.67
Hs Code.:

tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

Synonyms:tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

There total 24 articles about tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-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:

: 2051-49-2
n-hexanoic anhydride

: 506442-03-1
tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 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

6: 0.90 g / MS 4 Angstroem; TMSOTf / 1,2-dichloro-ethane / 8 h / 20 °C

7: Zn/Cd; AcOH / 2 h / sonication

8: 0.43 g / pyridine / CH₂Cl₂ / 2 h

With pyridine; 1H-imidazole; methanol; dmap; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; hydrogen fluoride; pyridinium p-toluenesulfonate; acetic acid; cadmium; zinc; In dichloromethane; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/ja0284456

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 506442-03-1
tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 69 percent / DMAP / CH₂Cl₂ / 20 °C

2: 5-phenyl-1H-tetrazole / CH₂Cl₂ / 2 h

3: 3.32 g / aq. magnesium monoperoxyphtalate hexahydrate / CH₂Cl₂ / 3 h

4: 74 percent / aq. HF / acetonitrile / 8 h

5: K₂CO₃ / 2 h

6: 0.90 g / MS 4 Angstroem; TMSOTf / 1,2-dichloro-ethane / 8 h / 20 °C

7: Zn/Cd; AcOH / 2 h / sonication

8: 0.43 g / pyridine / CH₂Cl₂ / 2 h

With pyridine; dmap; 5-Phenyl-1H-tetrazole; magnesium bis(monoperoxyphthalate)hexahydrate; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; hydrogen fluoride; potassium carbonate; acetic acid; cadmium; zinc; In dichloromethane; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/ja0284456

Reference yield:

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

: 506442-03-1
tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 13 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

11: 0.90 g / MS 4 Angstroem; TMSOTf / 1,2-dichloro-ethane / 8 h / 20 °C

12: Zn/Cd; AcOH / 2 h / sonication

13: 0.43 g / pyridine / CH₂Cl₂ / 2 h

With pyridine; 1H-imidazole; methanol; dmap; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; hydrogen fluoride; ammonia; pyridinium p-toluenesulfonate; acetic acid; ethylenediamine; cadmium; zinc; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/ja0284456