ethyl (4R,5S)-5-azide-6-(tert-butyldiphenylsilyloxy)-4-ethyl-2-hexenoate

Base Information

Chemical Name:ethyl (4R,5S)-5-azide-6-(tert-butyldiphenylsilyloxy)-4-ethyl-2-hexenoate
CAS No.:442202-36-0
Molecular Formula:C₂₆H₃₅N₃O₃Si
Molecular Weight:465.668
Hs Code.:

Synonyms:ethyl (4R,5S)-5-azide-6-(tert-butyldiphenylsilyloxy)-4-ethyl-2-hexenoate

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Chemical Property of ethyl (4R,5S)-5-azide-6-(tert-butyldiphenylsilyloxy)-4-ethyl-2-hexenoate

Chemical Property:

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Technology Process of ethyl (4R,5S)-5-azide-6-(tert-butyldiphenylsilyloxy)-4-ethyl-2-hexenoate

There total 10 articles about ethyl (4R,5S)-5-azide-6-(tert-butyldiphenylsilyloxy)-4-ethyl-2-hexenoate 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:

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

: 442202-36-0
ethyl (4R,5S)-5-azide-6-(tert-butyldiphenylsilyloxy)-4-ethyl-2-hexenoate

Guidance literature:: Multi-step reaction with 11 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

9.1: PPTS / ethanol / 2 h / 60 °C

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

11.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

11.2: 935 mg / tetrahydrofuran / 2 h / 20 °C

With dmap; potassium osmate(VI); n-butyllithium; sodium azide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Swern oxidation / 4.2: Wittig reaction / 10.1: Swern oxidation / 11.2: Horner-Emmons reaction;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

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

: 442202-36-0
ethyl (4R,5S)-5-azide-6-(tert-butyldiphenylsilyloxy)-4-ethyl-2-hexenoate

Guidance literature:: Multi-step reaction with 8 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

6.1: PPTS / ethanol / 2 h / 60 °C

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

8.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

8.2: 935 mg / tetrahydrofuran / 2 h / 20 °C

With dmap; potassium osmate(VI); n-butyllithium; sodium azide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.2: Wittig reaction / 7.1: Swern oxidation / 8.2: Horner-Emmons reaction;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

: 442202-32-6
(2S)-2-(2-ethylbut-3-enyloxy)tetrahydropyrane

: 442202-36-0
ethyl (4R,5S)-5-azide-6-(tert-butyldiphenylsilyloxy)-4-ethyl-2-hexenoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 80 percent / (DHQD)2PYR; K₂OsO₄*2H₂O; K₃Fe(CN)6 / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

2.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

3.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: 1.3 g / NaN₃ / dimethylformamide / 15 h / 80 °C

5.1: PPTS / ethanol / 2 h / 60 °C

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

7.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

7.2: 935 mg / tetrahydrofuran / 2 h / 20 °C

With dmap; potassium osmate(VI); sodium azide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: Swern oxidation / 7.2: Horner-Emmons reaction;
DOI:10.1016/j.tet.2004.05.039