2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone

Base Information

Chemical Name:2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone
CAS No.:336130-14-4
Molecular Formula:C₃₄H₅₅N₃O₅Si₃
Molecular Weight:670.084
Hs Code.:

Synonyms:2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone

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Chemical Property of 2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone

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Technology Process of 2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone

There total 5 articles about 2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-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:

: 336130-11-1
1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose

: 336130-14-4
2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone

Guidance literature:: Multi-step reaction with 3 steps

1: PhI(OAc)2; n-Bu₄NN₃

2: aq. Hg(OCOCF₃)2 / tetrahydrofuran

3: PCC; NaOAc / CH₂Cl₂

With [bis(acetoxy)iodo]benzene; sodium acetate; mercury(II) trifluoroacetate; tetrabutylammoniun azide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2004.09.091

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 336130-14-4
2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / pyridine / tetrahydrofuran / 24.5 h / 0 - 20 °C

2.1: 80 percent / H₂O; PPh₃*HBr / tetrahydrofuran / 6 h / 20 °C

3.1: 92 percent / PCC; NaOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

4.1: KHMDS / tetrahydrofuran / 0.75 h / -78 °C

4.2: trisyl-N₃ / tetrahydrofuran / 0.08 h / -96 °C

4.3: 56 percent / AcOH / tetrahydrofuran / 1 h / -96 - 20 °C

With pyridine; 4 A molecular sieve; water; sodium acetate; triphenylphosphine hydrobromide; potassium hexamethylsilazane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo001512z

Reference yield:

: 87316-22-1,137893-35-7
1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enitol

: 336130-14-4
2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / pyridine / tetrahydrofuran / 24.5 h / 0 - 20 °C

2.1: 80 percent / H₂O; PPh₃*HBr / tetrahydrofuran / 6 h / 20 °C

3.1: 92 percent / PCC; NaOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

4.1: KHMDS / tetrahydrofuran / 0.75 h / -78 °C

4.2: trisyl-N₃ / tetrahydrofuran / 0.08 h / -96 °C

4.3: 56 percent / AcOH / tetrahydrofuran / 1 h / -96 - 20 °C

With pyridine; 4 A molecular sieve; water; sodium acetate; triphenylphosphine hydrobromide; potassium hexamethylsilazane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo001512z