tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside
CAS No.:1203582-46-0
Molecular Formula:C₅₆H₆₄N₄O₁₂Si
Molecular Weight:1013.23
Hs Code.:

tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside

Synonyms:tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside

There total 5 articles about tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-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: 26.0%

: 367518-26-1
trichloroacetoimidoyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α/β-D-glucopyranoside

: 514792-62-2
3,6-di-O-benzyl-1-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 1203582-46-0
tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside

: tert-butyldimethylsilyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 1h; diastereoselective reaction;
DOI:10.1007/s00706-009-0172-0

Reference yield:

: 732246-93-4
(tert-butyl)dimethylsilyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

: 1203582-46-0
tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside

: tert-butyldimethylsilyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / 1,4-dioxane / 13 h / 30 °C / 30 Torr

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 0 - 20 °C

3.1: triethylsilane; trifluoroacetic acid / dichloromethane / 0 - 20 °C

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -20 °C

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; mineral oil;
DOI:10.1007/s00706-009-0172-0

Reference yield:

: 459170-35-5
tert-butyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 1203582-46-0
tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside

: tert-butyldimethylsilyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

1.2: 0 - 20 °C

2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 0 - 20 °C

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -20 °C

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; mineral oil;
DOI:10.1007/s00706-009-0172-0