2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(acetyloxy)methyl]-1-deoxy-1-phenylsulfinyl-β-D-glucopyranoside

Base Information

Chemical Name:2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(acetyloxy)methyl]-1-deoxy-1-phenylsulfinyl-β-D-glucopyranoside
CAS No.:1352407-01-2
Molecular Formula:C₂₅H₂₈O₉S
Molecular Weight:504.558
Hs Code.:

Synonyms:2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(acetyloxy)methyl]-1-deoxy-1-phenylsulfinyl-β-D-glucopyranoside

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Chemical Property of 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(acetyloxy)methyl]-1-deoxy-1-phenylsulfinyl-β-D-glucopyranoside

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Technology Process of 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(acetyloxy)methyl]-1-deoxy-1-phenylsulfinyl-β-D-glucopyranoside

There total 5 articles about 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(acetyloxy)methyl]-1-deoxy-1-phenylsulfinyl-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: 98.0%

: 1352407-00-1
1-deoxy-4,6-O-benzylidene-3-O-methyl-5-C-hydroxymethyl-1-phenyl-sulfinyl-β-D-glucopyranoside

: 108-24-7
acetic anhydride

: 1352407-01-2
2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(acetyloxy)methyl]-1-deoxy-1-phenylsulfinyl-β-D-glucopyranoside

Guidance literature:: With pyridine; at 20 ℃; for 23h; Inert atmosphere;
DOI:10.1016/j.bmcl.2011.10.005

Reference yield:

: 1352406-91-7
phenyl 2,4,6-tri-O-acetyl-3-O-methyl-5-C-vinyl-1-thio-β-D-glucopyranoside

: 1352407-01-2
2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(acetyloxy)methyl]-1-deoxy-1-phenylsulfinyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium methylate / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

1.2: IR-120 H⁺ resin / 0.75 h / 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 3 h / 70 °C / Inert atmosphere

3.1: ozone / dichloromethane / 0.05 h / -78 °C

4.1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C

5.1: pyridine / 23 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; sodium methylate; toluene-4-sulfonic acid; ozone; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2011.10.005

Reference yield:

: 1352406-92-8
phenyl 4,6-O-benzylidene-3-O-methyl-5-C-vinyl-1-thio-β-D-glucopyranoside

: 1352407-01-2
2-O-acetyl-4,6-O-benzylidene-3-O-methyl-5-C-[1-(acetyloxy)methyl]-1-deoxy-1-phenylsulfinyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: ozone / dichloromethane / 0.05 h / -78 °C

2: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C

3: pyridine / 23 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; ozone; In ethanol; dichloromethane;
DOI:10.1016/j.bmcl.2011.10.005