Alanine, 3-(hydroxydimethylsilyl)-

Base Information

• Chemical Name: Alanine, 3-(hydroxydimethylsilyl)-
• CAS No.: 850755-38-3
• Molecular Formula: C₅H₁₃NO₃Si
• Molecular Weight: 163.249
• Mol file: 850755-38-3.mol

Synonyms:

Chemical Property of Alanine, 3-(hydroxydimethylsilyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Alanine, 3-(hydroxydimethylsilyl)-

There total 10 articles about Alanine, 3-(hydroxydimethylsilyl)- 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: 98.0%

(R)-2-azido-3-[(azidomethyl)dimethylsilyl]propanoic acid (770738-47-1) → (R)-2-amino-3-[hydroxydimethylsilyl]propanoic acid (770738-48-2,850755-38-3)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; water; at 23 ℃; for 14h; under 760 Torr;

DOI:10.1002/hlca.200490152

Reference yield:

3-[(chloromethyl)(dimethyl)silyl]propanoic acid (770738-34-6) → (R)-2-amino-3-[hydroxydimethylsilyl]propanoic acid (770738-48-2,850755-38-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pivaloyl chloride; NaH / tetrahydrofuran / 2 h

1.2: 84 percent / BuLi / tetrahydrofuran; hexane / 4 h / -78 - 23 °C

2.1: 97 percent / NaI / acetone / 48 h / 65 °C

3.1: 94 percent / N,N,N',N'-tetramethylguanidinium azide / acetonitrile / 48 h / 23 °C

4.1: EtN(iPr)2; Bu₂BOTf / CH₂Cl₂ / 4 h / 0 °C

4.2: 62 percent / NBS / CH₂Cl₂ / 1 h / -78 °C

5.1: N,N,N',N'-tetramethylguanidinium azide / acetonitrile / 4 h / 0 °C

6.1: 99 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 0 °C

7.1: 98 percent / H₂ / PtO₂*H₂O / ethanol; H₂O / 14 h / 23 °C / 760 Torr

With lithium hydroxide; N,N,N',N'-tetramethylguanidinium azide; di-n-butylboryl trifluoromethanesulfonate; hydrogen; pivaloyl chloride; sodium hydride; N-ethyl-N,N-diisopropylamine; sodium iodide; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; acetonitrile; 2.1: Finkelstein reaction;

DOI:10.1002/hlca.200490152

Reference yield:

(R)-4-benzyl-3-{3-[(chloromethyl)dimethylsilyl]propanoyl}-1,3-oxazolidin-2-one (770738-35-7) → (R)-2-amino-3-[hydroxydimethylsilyl]propanoic acid (770738-48-2,850755-38-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / NaI / acetone / 48 h / 65 °C

2.1: 94 percent / N,N,N',N'-tetramethylguanidinium azide / acetonitrile / 48 h / 23 °C

3.1: EtN(iPr)2; Bu₂BOTf / CH₂Cl₂ / 4 h / 0 °C

3.2: 62 percent / NBS / CH₂Cl₂ / 1 h / -78 °C

4.1: N,N,N',N'-tetramethylguanidinium azide / acetonitrile / 4 h / 0 °C

5.1: 99 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 0 °C

6.1: 98 percent / H₂ / PtO₂*H₂O / ethanol; H₂O / 14 h / 23 °C / 760 Torr

With lithium hydroxide; N,N,N',N'-tetramethylguanidinium azide; di-n-butylboryl trifluoromethanesulfonate; hydrogen; N-ethyl-N,N-diisopropylamine; sodium iodide; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; acetonitrile; 1.1: Finkelstein reaction;

DOI:10.1002/hlca.200490152

upstream raw materials:

(R)-2-azido-3-[(azidomethyl)dimethylsilyl]propanoic acid

3-[(chloromethyl)(dimethyl)silyl]propanoic acid

(R)-4-benzyl-3-{3-[(chloromethyl)dimethylsilyl]propanoyl}-1,3-oxazolidin-2-one

(R)-4-benzyl-3-{3-[(iodomethyl)dimethylsilyl]propanoyl}-1,3-oxazolidin-2-one

Refernces