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

Base Information

• Chemical Name: tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside
• CAS No.: 506442-02-0
• Molecular Formula: C₆₉H₉₄Cl₃N₂O₂₁PSi
• Molecular Weight: 1452.92
• Mol file: 506442-02-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-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:

tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside (506441-97-0) + Hexanoic acid (2R,3S,4R,5R)-2-benzyloxycarbonyloxymethyl-3-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester → tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside (506442-02-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; In 1,2-dichloro-ethane; at 20 ℃; for 8h;

DOI:10.1021/ja0284456

Reference yield:

n-hexanoic anhydride (2051-49-2) → tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside (506442-02-0)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; 1H-imidazole; methanol; dmap; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; hydrogen fluoride; pyridinium p-toluenesulfonate; In dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/ja0284456

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside (506442-02-0)

Guidance literature:

Multi-step reaction with 6 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

With dmap; 5-Phenyl-1H-tetrazole; magnesium bis(monoperoxyphthalate)hexahydrate; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; hydrogen fluoride; potassium carbonate; In dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/ja0284456

upstream raw materials:

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

n-hexanoic anhydride

benzyl chloroformate

2-Desoxy-2-hexanoylamino-D-glucose

Downstream raw materials:

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