(S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)propan-2-ol

Base Information

• Chemical Name: (S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)propan-2-ol
• CAS No.: 127744-29-0
• Molecular Formula: C₁₆H₂₈O₃Si
• Molecular Weight: 296.482
• Mol file: 127744-29-0.mol

Synonyms:(S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)propan-2-ol

Chemical Property of (S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)propan-2-ol

There total 6 articles about (S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)propan-2-ol 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%

(R)-3-benzyloxy-1,2-propanediol (56552-80-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)propan-2-ol (127744-29-0)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 19h; regioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.202101055

Reference yield:

O-Benzyl-L-serine (4726-96-9,32520-12-0) → (S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)propan-2-ol (127744-29-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NaNO₂, H₂SO₄ / 16 h / Ambient temperature

2: 70 percent / H+

3: LiAlH₄ / tetrahydrofuran

4: 83 percent / Et₃N / CH₂Cl₂

With lithium aluminium tetrahydride; sulfuric acid; hydrogen cation; triethylamine; sodium nitrite; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)80605-5

Reference yield:

(S)-3-(benzyloxy)-2-hydroxypropanoic acid (130111-08-9,127744-27-8) → (S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)propan-2-ol (127744-29-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / H+

2: LiAlH₄ / tetrahydrofuran

3: 83 percent / Et₃N / CH₂Cl₂

With lithium aluminium tetrahydride; hydrogen cation; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)80605-5

upstream raw materials:

(R)-3-benzyloxy-1,2-propanediol

tert-butyldimethylsilyl chloride

O-Benzyl-L-serine

(S)-3-(benzyloxy)-2-hydroxypropanoic acid

Downstream raw materials:

(S)-benzyl glycidyl ether

(R)-2-[1-benzyloxymethyl-2-(tert-butyldimethylsilanyloxy)ethoxy]isoindole-1,3-dione

(R)-3-(benzyloxy)-2-(hexadecyloxy)propan-1-ol

3-O-benzyl-1-O-hexadecanoyl-2-O-hexadecyl-sn-glycerol