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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone
CAS No.:769147-50-4
Molecular Formula:C₅₂H₆₈N₂O₂₀Si
Molecular Weight:1069.2
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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Synonyms: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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

There total 5 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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-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: 63.0%

: 108-24-7
acetic anhydride

: 769147-25-3
C₅₄H₆₆Cl₆N₂O₂₂Si

: 769147-50-4
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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Guidance literature:: With zinc; at 20 ℃; for 24h;
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

: 769147-50-4
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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Guidance literature:: Multi-step reaction with 3 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

With trimethylsilyl trifluoromethanesulfonate; zinc; In 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

: 769147-50-4
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)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Guidance literature:: Multi-step reaction with 4 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

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