3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate

Base Information

Chemical Name:3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate
CAS No.:886852-54-6
Molecular Formula:C₁₆H₂₃N₃O₇S
Molecular Weight:401.441
Hs Code.:

Synonyms:3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate

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Chemical Property of 3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate

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Technology Process of 3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate

There total 11 articles about 3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate 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: 95.0%

: 886852-63-7
3-((2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2H-pyran-2-yl)propyl methanesulfonate

: 886852-54-6
3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate

Guidance literature:: With water; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In acetone; tert-butyl alcohol; for 24h;
DOI:10.1021/ol0602811

Reference yield:

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

: 886852-54-6
3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate

Guidance literature:: Multi-step reaction with 8 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

6: 99 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

7: 99 percent / triethylamine / CH₂Cl₂ / 0.5 h

8: 95 percent / N-methylmorpholine N-oxide; water / OsO₄ / 2-methyl-propan-2-ol; acetone / 24 h

With pyridine; dmap; sodium tetrahydroborate; trimethylsilylazide; tetrabutyl ammonium fluoride; water; 4-methylmorpholine N-oxide; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; methanol; dichloromethane; acetone; tert-butyl alcohol; 3: Luche reduction;
DOI:10.1021/ol0602811

Reference yield:

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

: 886852-54-6
3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate

Guidance literature:: Multi-step reaction with 9 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

7: 99 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

8: 99 percent / triethylamine / CH₂Cl₂ / 0.5 h

9: 95 percent / N-methylmorpholine N-oxide; water / OsO₄ / 2-methyl-propan-2-ol; acetone / 24 h

With pyridine; dmap; sodium tetrahydroborate; N-Bromosuccinimide; trimethylsilylazide; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II)); sodium acetate; triphenylphosphine; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; methanol; dichloromethane; acetone; tert-butyl alcohol; 1: Achmatowicz reaction / 4: Luche reduction;
DOI:10.1021/ol0602811