prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Base Information

Chemical Name:prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone
CAS No.:769147-65-1
Molecular Formula:C₄₃H₅₆N₂O₂₂S
Molecular Weight:984.984
Hs Code.:

prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

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Chemical Property of prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

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Technology Process of prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

There total 7 articles about prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone 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: 52.0%

: 98-59-9
p-toluenesulfonyl chloride

: 769147-29-7
prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

: 769147-65-1
prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Guidance literature:: With pyridine; dmap; at 20 ℃;
DOI:10.1002/hlca.200490161

Reference yield:

: 769147-47-9
3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-4-O-{3,4,6-tri-O-acetyl-2-deoxy-2-{[(2,2,2-trichloroethoxy)carbonyl]amino}-β-D-glucopyranosyl}-2-{[(2,2,2-trichloroethoxy)carbonyl]amino}-α-D-glucopyranose

: 769147-65-1
prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Guidance literature:: Multi-step reaction with 5 steps

1.1: CH₂Cl₂ / 1 h / 20 °C

1.2: 88 percent / Cs₂CO₃ / CH₂Cl₂ / 4.5 h / 20 °C

2.1: 55 percent / Me₃SiOTf / 1,2-dichloro-ethane / 0.75 h / -30 °C

3.1: 63 percent / Zn / 24 h / 20 °C

4.1: 43 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

5.1: 52 percent / pyridine; DMAP / 20 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; zinc; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1002/hlca.200490161

Reference yield:

: 769147-45-7
(tert-butyl)dimethylsilyl 3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-4-O-{3,4,6-tri-O-acetyl-2-deoxy-2-{[(2,2,2-trichloroethoxy)carbonyl]amino}-β-D-glucopyranosyl}-2-{[(2,2,2-trichloroethoxy)carbonyl]amino}-β-D-glucopyranoside

: 769147-65-1
prop-2-enyl O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-2-deoxy-6-O-tosyl-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 55 percent / [PdCl₂(MeCN)2] / acetone / 96 h / 20 °C

2.1: CH₂Cl₂ / 1 h / 20 °C

2.2: 88 percent / Cs₂CO₃ / CH₂Cl₂ / 4.5 h / 20 °C

3.1: 55 percent / Me₃SiOTf / 1,2-dichloro-ethane / 0.75 h / -30 °C

4.1: 63 percent / Zn / 24 h / 20 °C

5.1: 43 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

6.1: 52 percent / pyridine; DMAP / 20 °C

With pyridine; dmap; dichloro bis(acetonitrile) palladium(II); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; zinc; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetone;
DOI:10.1002/hlca.200490161