1'-(4',6'-O-benzylidene-3'-O-methyl-5'-C-[1-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine

Base Information

Chemical Name:1'-(4',6'-O-benzylidene-3'-O-methyl-5'-C-[1-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine
CAS No.:1352407-04-5
Molecular Formula:C₂₇H₃₀N₂O₁₀S
Molecular Weight:574.609
Hs Code.:

Synonyms:1'-(4',6'-O-benzylidene-3'-O-methyl-5'-C-[1-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine

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Chemical Property of 1'-(4',6'-O-benzylidene-3'-O-methyl-5'-C-[1-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine

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Technology Process of 1'-(4',6'-O-benzylidene-3'-O-methyl-5'-C-[1-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine

There total 10 articles about 1'-(4',6'-O-benzylidene-3'-O-methyl-5'-C-[1-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine 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: 62.0%

: 1352407-03-4
1'-(4',6'-O-benzylidene-3'-O-methyl-5'-C-hydroxymethyl-β-D-glucopyranosyl)thymine

: 98-59-9
p-toluenesulfonyl chloride

: 1352407-04-5
1'-(4',6'-O-benzylidene-3'-O-methyl-5'-C-[1-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine

Guidance literature:: With pyridine; at 20 - 60 ℃; for 20h; 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

: 1352407-04-5
1'-(4',6'-O-benzylidene-3'-O-methyl-5'-C-[1-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine

Guidance literature:: Multi-step reaction with 8 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

6.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 20 h / 20 °C

7.1: methanol; ammonia / 7 h / 20 °C

8.1: pyridine / 20 h / 20 - 60 °C / Inert atmosphere

With pyridine; methanol; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; ammonia; sodium methylate; toluene-4-sulfonic acid; ozone; In methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 6.1: Vorbrüggen coupling;
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

: 1352407-04-5
1'-(4',6'-O-benzylidene-3'-O-methyl-5'-C-[1-(tosyloxy)methyl]-β-D-glucopyranosyl)thymine

Guidance literature:: Multi-step reaction with 6 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

4: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 20 h / 20 °C

5: methanol; ammonia / 7 h / 20 °C

6: pyridine / 20 h / 20 - 60 °C / Inert atmosphere

With pyridine; methanol; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; ammonia; ozone; In ethanol; dichloromethane; 1,2-dichloro-ethane; 4: Vorbrüggen coupling;
DOI:10.1016/j.bmcl.2011.10.005