1-thiophenyl-6-O-tosyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside

Base Information

Chemical Name:1-thiophenyl-6-O-tosyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside
CAS No.:1345978-70-2
Molecular Formula:C₃₂H₃₆O₁₂S₂
Molecular Weight:676.763
Hs Code.:

Synonyms:1-thiophenyl-6-O-tosyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside

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Chemical Property of 1-thiophenyl-6-O-tosyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside

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Technology Process of 1-thiophenyl-6-O-tosyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside

There total 5 articles about 1-thiophenyl-6-O-tosyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-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: 76.0%

: 1032959-15-1
1-thiophenyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside

: 98-59-9
p-toluenesulfonyl chloride

: 1345978-70-2
1-thiophenyl-6-O-tosyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside

Guidance literature:: With pyridine; at 20 ℃; for 12h;
DOI:10.1039/c1ob06085f

Reference yield:

: 20764-63-0
β-cellobioseoctaacetate

: 1345978-70-2
1-thiophenyl-6-O-tosyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: boron trifluoride diethyl etherate / dichloromethane / 6 h / 0 °C / Inert atmosphere

2: methanol; sodium methylate / 2 h / 20 °C

3: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / N,N-dimethyl-formamide / 2 h / 60 °C

4: pyridine / 12 h / 20 °C

With pyridine; methanol; boron trifluoride diethyl etherate; sodium methylate; [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; In dichloromethane; N,N-dimethyl-formamide; 3: Zemplen deacetylation;
DOI:10.1039/c1ob06085f

Reference yield:

: 28022-14-2
phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside

: 1345978-70-2
1-thiophenyl-6-O-tosyl-4-O-(4',6'-O-benzylidiene-β-D-glucopyranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: methanol; sodium methylate / 2 h / 20 °C

2: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / N,N-dimethyl-formamide / 2 h / 60 °C

3: pyridine / 12 h / 20 °C

With pyridine; methanol; sodium methylate; [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; In N,N-dimethyl-formamide; 2: Zemplen deacetylation;
DOI:10.1039/c1ob06085f