(1'S,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole

Base Information

• Chemical Name: (1'S,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole
• CAS No.: 169905-33-3
• Molecular Formula: C₂₃H₃₆N₂O₃SSi
• Molecular Weight: 448.702
• Mol file: 169905-33-3.mol

Synonyms:(1'S,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole

Chemical Property of (1'S,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole

There total 11 articles about (1'S,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole 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: 96.0%

(S,S)-2-<2--1-hydroxy-3-phenylpropyl>-1,3-thiazole (124127-20-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (1'S,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole (169905-33-3)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1021/jo00129a057

Reference yield: 76.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (S)-2(tert-butoxycarbonyl)amino-3-phenyl-(R)-1-(2-thiazolyl)propan-1-ol (129776-83-6) → (1'S,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole (169905-33-3) + (1'R,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole (172329-47-4)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 18h; Yield given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00129a037

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (1'S,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole (169905-33-3)

Guidance literature:

Multi-step reaction with 10 steps

1: LAH / tetrahydrofuran / 1 h / Heating

2: molecular sieves 4 Angstroem / toluene / 1 h / 90 °C

3: NaBH₄ / methanol / 30 h / 0 °C

4: 99 percent / dioxane / 18 h / Ambient temperature

5: 1.) (COCl)2, DMSO, 2.) diisopropylethylamine / 1.) CH₂Cl₂, - 60 deg C to -45 deg C, 30 min; -45 deg C, 5 min, 2.) 5 min

6: 2.) Bu₄NF*3H₂O / 1.) CH₂Cl₂, -20 deg C, 48 h, 2.) THF, r.t., 1 h

7: 99 percent / pyridine, DMAP / 18 h / Ambient temperature

8: CAN / acetonitrile; H₂O / 18 h / Ambient temperature

9: CH₃ONa / methanol / 0.25 h / Ambient temperature

10: 96 percent / imidazole, DMAP / dimethylformamide / 18 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; ammonium cerium(IV) nitrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00129a057

upstream raw materials:

(S,S)-2-<2--1-hydroxy-3-phenylpropyl>-1,3-thiazole

tert-butyldimethylsilyl chloride

(S)-2(tert-butoxycarbonyl)amino-3-phenyl-(R)-1-(2-thiazolyl)propan-1-ol

L-phenylalanine

Downstream raw materials:

(2S,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal