(2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran

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Chemical Name:(2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran
CAS No.:886852-55-7
Molecular Formula:C₂₁H₃₃N₃O₃Si
Molecular Weight:403.597
Hs Code.:

Synonyms:(2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran

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Chemical Property of (2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran

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Technology Process of (2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran

There total 8 articles about (2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran 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%

: 886852-61-5
(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-yl methyl carbonate

: 886852-55-7
(2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran

Guidance literature:: With trimethylsilylazide; bis(η3-allyl-μ-chloropalladium(II)); 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; at 50 ℃; for 24h;
DOI:10.1021/ol0602811

Reference yield:

: 886852-56-8
(2S)-6-hydroxy-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3(6H)-one

: 886852-55-7
(2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / DMAP / CH₂Cl₂ / 14 h / -78 °C

2: 88 percent / Pd₂(DBA)3*CHCl₃; triphenylphosphine / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 94 percent / NaBH₄ / CH₂Cl₂; methanol / 4 h / -78 °C

4: 72 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 20 °C

5: 77 percent / TMSN₃ / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 24 h / 50 °C

With pyridine; dmap; sodium tetrahydroborate; trimethylsilylazide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; methanol; dichloromethane; 3: Luche reduction;
DOI:10.1021/ol0602811

Reference yield:

: 886852-57-9
(S)-1-(furan-2-yl)-4-tert-butyldimethylsilyloxybutan-1-ol

: 886852-55-7
(2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / NBS; H₂O; NaHCO₃ / NaOAc*3H₂O / tetrahydrofuran / 0.5 h / 0 °C

2: 85 percent / DMAP / CH₂Cl₂ / 14 h / -78 °C

3: 88 percent / Pd₂(DBA)3*CHCl₃; triphenylphosphine / CH₂Cl₂ / 2 h / 0 - 20 °C

4: 94 percent / NaBH₄ / CH₂Cl₂; methanol / 4 h / -78 °C

5: 72 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 20 °C

6: 77 percent / TMSN₃ / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 24 h / 50 °C

With pyridine; dmap; sodium tetrahydroborate; N-Bromosuccinimide; trimethylsilylazide; water; sodium hydrogencarbonate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; bis(η3-allyl-μ-chloropalladium(II)); sodium acetate; triphenylphosphine; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; methanol; dichloromethane; 1: Achmatowicz reaction / 4: Luche reduction;
DOI:10.1021/ol0602811