2-trimethylsilylethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl

Base Information

Chemical Name:2-trimethylsilylethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl
CAS No.:904690-76-2
Molecular Formula:C₃₉H₅₃NO₁₄Si
Molecular Weight:787.934
Hs Code.:

Synonyms:2-trimethylsilylethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl

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Chemical Property of 2-trimethylsilylethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl

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Technology Process of 2-trimethylsilylethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl

There total 15 articles about 2-trimethylsilylethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl 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:

: (2R,3R,4S,5R,6S)-5-Benzyloxy-6-methyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,4-diol

: 904690-76-2
2-trimethylsilylethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl

Guidance literature:: Multi-step reaction with 8 steps

1: 141 g / camphorsulfonic acid / CH₂Cl₂ / 2 h / 22 °C

2: 82 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 5 h / 0 - 22 °C

3: AcOH; aq. HCl / 0.33 h / 22 °C

4: 13.5 g / 4-dimethylaminopyridine / pyridine / 1 h / 22 °C

5: 92 percent / thiourea; pyridine / dimethylformamide / 2 h / 22 °C

6: 95 percent / 4-dimethylaminopyridine / pyridine / 1 h / 22 °C

7: hydrogen; Et₃N / Pd/C / ethanol / 12 h / 22 °C / 10343 Torr

8: 2.70 g / 4-dimethylaminopyridine / 2 h / 22 °C

With pyridine; hydrogenchloride; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; acetic acid; triethylamine; thiourea; palladium on activated charcoal; In pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2006.04.006

Reference yield:

: 904690-70-6
2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside

: 904690-76-2
2-trimethylsilylethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl

Guidance literature:: Multi-step reaction with 9 steps

1: AcOH / H₂O / 2 h / 65 °C

2: 141 g / camphorsulfonic acid / CH₂Cl₂ / 2 h / 22 °C

3: 82 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 5 h / 0 - 22 °C

4: AcOH; aq. HCl / 0.33 h / 22 °C

5: 13.5 g / 4-dimethylaminopyridine / pyridine / 1 h / 22 °C

6: 92 percent / thiourea; pyridine / dimethylformamide / 2 h / 22 °C

7: 95 percent / 4-dimethylaminopyridine / pyridine / 1 h / 22 °C

8: hydrogen; Et₃N / Pd/C / ethanol / 12 h / 22 °C / 10343 Torr

9: 2.70 g / 4-dimethylaminopyridine / 2 h / 22 °C

With pyridine; hydrogenchloride; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; acetic acid; triethylamine; thiourea; palladium on activated charcoal; In pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2006.04.006

Reference yield:

: 904690-67-1
phenyl 2-azido-2-deoxy-4,6-O-diphenylmethylidene-1-thio-β-D-glucopyranoside

: 904690-76-2
2-trimethylsilylethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / 2,4,6-tri-tert-butylpyrimidine / CH₂Cl₂ / 1 h / 0 °C

2: 82 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 5 h / 0 - 22 °C

3: AcOH; aq. HCl / 0.33 h / 22 °C

4: 13.5 g / 4-dimethylaminopyridine / pyridine / 1 h / 22 °C

5: 92 percent / thiourea; pyridine / dimethylformamide / 2 h / 22 °C

6: 95 percent / 4-dimethylaminopyridine / pyridine / 1 h / 22 °C

7: hydrogen; Et₃N / Pd/C / ethanol / 12 h / 22 °C / 10343 Torr

8: 2.70 g / 4-dimethylaminopyridine / 2 h / 22 °C

With pyridine; hydrogenchloride; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; hydrogen; acetic acid; triethylamine; thiourea; 2,4,6-tri-tert-butylpyrimidine; palladium on activated charcoal; In pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2006.04.006