(2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-azide

Base Information

Chemical Name:(2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-azide
CAS No.:442202-35-9
Molecular Formula:C₂₇H₃₉N₃O₃Si
Molecular Weight:481.71
Hs Code.:

Synonyms:(2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-azide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-azide

Chemical Property:

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Technology Process of (2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-azide

There total 10 articles about (2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-azide 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:

: Methanesulfonic acid (1R,2R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(tetrahydro-pyran-2-yloxymethyl)-butyl ester

: 442202-35-9
(2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-azide

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 15h;
DOI:10.1021/ol025775m DOI:10.1016/j.tet.2004.05.039

Reference yield:

: 117935-51-0
(R)-1-O-acetyl-2-ethyl-1,3-propanediol

: 442202-35-9
(2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-azide

Guidance literature:: Multi-step reaction with 8 steps

1.1: PPTS / CH₂Cl₂ / 2 h / 20 °C

2.1: K₂CO₃ / methanol / 3 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: 695 mg / tetrahydrofuran; hexane / 1.5 h / 20 °C

5.1: 80 percent / (DHQD)2PYR; K₂OsO₄*2H₂O; K₃Fe(CN)6 / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

6.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

7.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

8.1: 1.3 g / NaN₃ / dimethylformamide / 15 h / 80 °C

With dmap; potassium osmate(VI); n-butyllithium; sodium azide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Swern oxidation / 4.2: Wittig reaction;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

: (R)-2-(Tetrahydro-pyran-2-yloxymethyl)-butyraldehyde

: 442202-35-9
(2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-azide

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

1.2: 695 mg / tetrahydrofuran; hexane / 1.5 h / 20 °C

2.1: 80 percent / (DHQD)2PYR; K₂OsO₄*2H₂O; K₃Fe(CN)6 / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

3.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

4.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

5.1: 1.3 g / NaN₃ / dimethylformamide / 15 h / 80 °C

With dmap; potassium osmate(VI); n-butyllithium; sodium azide; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; triethylamine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.2: Wittig reaction;
DOI:10.1016/j.tet.2004.05.039