(2S,3S)-2-Azido-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

Base Information

Chemical Name:(2S,3S)-2-Azido-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester
CAS No.:866555-11-5
Molecular Formula:C₂₃H₃₁N₃O₃Si
Molecular Weight:425.603
Hs Code.:

Synonyms:(2S,3S)-2-Azido-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

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Chemical Property of (2S,3S)-2-Azido-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

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Technology Process of (2S,3S)-2-Azido-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

There total 9 articles about (2S,3S)-2-Azido-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester 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:

: 886442-76-8
(2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-2-trifluoromethanesulfonyloxy-pentanoic acid methyl ester

: 866555-11-5
(2S,3S)-2-Azido-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 25 ℃; for 0.666667h;
DOI:10.1002/anie.200500702

Reference yield:

: 88158-68-3
4-(tert-butyldiphenylsilyloxy)-1-butyne

: 866555-11-5
(2S,3S)-2-Azido-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi / diethyl ether; hexane / 1 h / -78 °C

1.2: 72 percent / diethyl ether; hexane / 18 h / 20 °C

2.1: 98 percent / H₂; quinoline / Pd/BaSO₄ / methanol / 0.67 h / 20 °C / 760 Torr

3.1: Ti(OiPr)4; L-diethyl tartrate; t-BuOOH / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 24 h / -20 °C

4.1: NaIO₄; RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 4 h / 20 °C

5.1: hexane / 40 h / 20 °C

6.1: K₂CO₃ / acetone / 18 h / 20 °C

7.1: pyridine / CH₂Cl₂ / 0.42 h / 0 °C

8.1: NaN₃ / dimethylformamide / 0.67 h / 20 °C

With pyridine; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium trichloride; sodium periodate; n-butyllithium; sodium azide; diethyl (2R,3R)-tartrate; hydrogen; potassium carbonate; Pd-BaSO₄; 4 A molecular sieve; In methanol; tetrachloromethane; diethyl ether; decane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 3.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ja060064v

Reference yield:

: 88159-03-9
5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol

: 866555-11-5
(2S,3S)-2-Azido-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / H₂; quinoline / Pd/BaSO₄ / methanol / 0.67 h / 20 °C / 760 Torr

2: Ti(OiPr)4; L-diethyl tartrate; t-BuOOH / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 24 h / -20 °C

3: NaIO₄; RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 4 h / 20 °C

4: hexane / 40 h / 20 °C

5: K₂CO₃ / acetone / 18 h / 20 °C

6: pyridine / CH₂Cl₂ / 0.42 h / 0 °C

7: NaN₃ / dimethylformamide / 0.67 h / 20 °C

With pyridine; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium trichloride; sodium periodate; sodium azide; diethyl (2R,3R)-tartrate; hydrogen; potassium carbonate; Pd-BaSO₄; 4 A molecular sieve; In methanol; tetrachloromethane; decane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 2: Sharpless asymmetric epoxidation;
DOI:10.1021/ja060064v