2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside

Base Information

Chemical Name:2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside
CAS No.:172360-96-2
Molecular Formula:C₃₃H₄₈O₁₆Si
Molecular Weight:728.82
Hs Code.:

Synonyms:2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside

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Chemical Property of 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside

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Technology Process of 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside

There total 4 articles about 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-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: 65.0%

: 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside

: 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-4-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside

: 172360-96-2
2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside

Guidance literature:: With sodium hydrogen sulfate; 18-crown-6 ether; 4 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; at 70 ℃;
DOI:10.1021/jo00127a042

Reference yield:

: 160533-98-2
2-(trimethylsilyl)ethyl 4-O-(4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside

: 172360-96-2
2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / Bu₄NCl, Bu₂SnO / toluene / 24 h / 35 °C

2: 87 percent / pyridine / 20 h / Ambient temperature

3: 85 percent / Bu₃SnH, AIBN / toluene / 23 h / Heating

4: 65 percent / DDQ, 18-crown-6, NaHSO₄, moist molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 70 °C

With pyridine; sodium hydrogen sulfate; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl-ammonium chloride; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; toluene;
DOI:10.1021/jo00127a042

Reference yield:

: 2-(Trimethylsilyl)ethyl 4-O-<3-O-<(phenylthio)(thiocarbonyl)>-4,6-O-(p-methoxybenzylidene)-β-D-galactopyranosyl>-β-D-glucopyranoside

: 172360-96-2
2-(Trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-<2-O-acetyl-3-deoxy-6-O-(p-methoxybenzoyl)-β-D-xylo-hexopyranosyl>-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / pyridine / 20 h / Ambient temperature

2: 85 percent / Bu₃SnH, AIBN / toluene / 23 h / Heating

3: 65 percent / DDQ, 18-crown-6, NaHSO₄, moist molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 70 °C

With pyridine; sodium hydrogen sulfate; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tri-n-butyl-tin hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; toluene;
DOI:10.1021/jo00127a042