(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

Base Information

• Chemical Name: (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
• CAS No.: 769147-45-7
• Molecular Formula: C₄₈H₆₆Cl₆N₂O₁₇Si₂
• Molecular Weight: 1211.94
• Mol file: 769147-45-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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: 77.0%

2,2,2-Trichloroethyl chloroformate (17341-93-4) + (tert-butyl)dimethylsilyl 3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranoside (768387-83-3) → (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 (769147-45-7)

Guidance literature:

(tert-butyl)dimethylsilyl 3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranoside; With ethylenediamine; In butan-1-ol; at 90 ℃; for 12h;

2,2,2-Trichloroethyl chloroformate; With sodium hydrogencarbonate; In methanol; water; at 20 ℃; for 1h;

With pyridine; acetic anhydride; In ethyl acetate; at 20 ℃;

DOI:10.1002/hlca.200490161

Reference yield: 55.0%

(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 (769147-45-7) → 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 (769147-47-9)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); In acetone; at 20 ℃; for 96h;

DOI:10.1002/hlca.200490161

Reference yield:

(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 (769147-45-7) → 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-6-O-tosyl-β-D-glucopyranosyl-(1->2)-3-O-(aminocarbonyl)-5-O-prop-2-enyl-β-D-glucofuranosiduronamide (769147-58-2)

Guidance literature:

Multi-step reaction with 8 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: 81 percent / NH₃ / tetrahydrofuran; methanol / 3 h / 0 °C

6.1: CH₂Cl₂ / 1 h / 20 °C

6.2: 96 percent / Zn / methanol / 3 h / 20 °C

7.1: 15 percent / Bu₄NF / tetrahydrofuran / 3 h / 20 °C

8.1: DMAP; pyridine / 20 °C

8.2: 14.6 percent / Zn / methanol / 3 h / 20 °C

With pyridine; dmap; dichloro bis(acetonitrile) palladium(II); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; ammonia; zinc; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; acetone;

DOI:10.1002/hlca.200490161

upstream raw materials:

2,2,2-Trichloroethyl chloroformate

(tert-butyl)dimethylsilyl 3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranoside

Downstream raw materials:

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

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

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-glucofuranosiduronamide

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}-1-O-(2,2,2-trichloro-1-iminoethyl)-α-D-glucopyranose