tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
CAS No.:132592-33-7
Molecular Formula:C₃₃H₄₁N₃O₆Si
Molecular Weight:603.791
Hs Code.:

Synonyms:tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 5 articles about tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-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: 90.0%

: 120312-09-6
tert-Butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid

: 98-88-4
benzoyl chloride

: 132592-33-7
tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: With dmap; triethylamine; In dichloromethane;
DOI:10.1021/jo00305a007

Reference yield:

: 99049-68-0
tert-Butyldimethylsilyl-2-azido-2-desoxy-4,6-O-isopropyliden-β-D-glucopyranosid

: 132592-33-7
tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / Bu₄NI, NaH / tetrahydrofuran / 5 h / 0 deg C to r.t.

2: 74 percent / TFA / tetrahydrofuran / 0.25 h / 0 °C

3: 1) (Bu₃Sn)2O, 2) Bu₄NBr / 1) toluene, reflux, 4h, 2) 80 deg C

4: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

With dmap; tetrabutylammomium bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; trifluoroacetic acid; bis(tri-n-butyltin)oxide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00008a040

Reference yield:

: 100-39-0
benzyl bromide

: 132592-33-7
tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / Bu₄NI, NaH / tetrahydrofuran / 5 h / 0 deg C to r.t.

2: 74 percent / TFA / tetrahydrofuran / 0.25 h / 0 °C

3: 1) (Bu₃Sn)2O, 2) Bu₄NBr / 1) toluene, reflux, 4h, 2) 80 deg C

4: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

With dmap; tetrabutylammomium bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; trifluoroacetic acid; bis(tri-n-butyltin)oxide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00008a040