(2S,3R)-2-benzyloxy-3,4-isopropylidenedioxy-1-(2-thiazolyl)-1-butanone

Base Information

• Chemical Name: (2S,3R)-2-benzyloxy-3,4-isopropylidenedioxy-1-(2-thiazolyl)-1-butanone
• CAS No.: 142705-77-9
• Molecular Formula: C₁₇H₁₉NO₄S
• Molecular Weight: 333.408
• Mol file: 142705-77-9.mol

Synonyms:(2S,3R)-2-benzyloxy-3,4-isopropylidenedioxy-1-(2-thiazolyl)-1-butanone

Chemical Property of (2S,3R)-2-benzyloxy-3,4-isopropylidenedioxy-1-(2-thiazolyl)-1-butanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-benzyloxy-3,4-isopropylidenedioxy-1-(2-thiazolyl)-1-butanone

There total 10 articles about (2S,3R)-2-benzyloxy-3,4-isopropylidenedioxy-1-(2-thiazolyl)-1-butanone 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: 88.0%

(1R,2R)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-thiazol-2-yl-ethanol (142760-41-6) → (2S,3R)-2-benzyloxy-3,4-isopropylidenedioxy-1-(2-thiazolyl)-1-butanone (142705-77-9)

Guidance literature:

With acetic anhydride; dimethyl sulfoxide; for 14h; Ambient temperature;

DOI:10.1055/s-1992-34170

Reference yield:

benzyl bromide (100-39-0) → (2S,3R)-2-benzyloxy-3,4-isopropylidenedioxy-1-(2-thiazolyl)-1-butanone (142705-77-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH, 2.) Bu₄NI / 1.) THF, reflux, 20 min, 2.) r. t., 14 h

2: acetonitrile / Heating

3: NaBH₄ / methanol / 0.5 h / Ambient temperature

4: HgCl₂ / acetonitrile; H₂O / 0.33 h / Ambient temperature

5: 2.) Bu₄NF / 1.) THF, r. t., 14 h, 2.) r. t., 2 h

6: 88 percent / DMSO, Ac₂O / 14 h / Ambient temperature

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; mercury dichloride; In methanol; water; acetonitrile;

DOI:10.1055/s-1992-34170

Reference yield:

((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-thiazol-2-yl-methanone (118319-71-4) → (2S,3R)-2-benzyloxy-3,4-isopropylidenedioxy-1-(2-thiazolyl)-1-butanone (142705-77-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / K-Selectride / tetrahydrofuran / 1 h / -78 °C

2: 1.) NaH, 2.) Bu₄NI / 1.) THF, reflux, 20 min, 2.) r. t., 14 h

3: acetonitrile / Heating

4: NaBH₄ / methanol / 0.5 h / Ambient temperature

5: HgCl₂ / acetonitrile; H₂O / 0.33 h / Ambient temperature

6: 2.) Bu₄NF / 1.) THF, r. t., 14 h, 2.) r. t., 2 h

7: 88 percent / DMSO, Ac₂O / 14 h / Ambient temperature

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium tri-sec-butyl-borohydride; dimethyl sulfoxide; mercury dichloride; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1055/s-1992-34170

upstream raw materials:

(1R,2R)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-thiazol-2-yl-ethanol

benzyl bromide

(S)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetaldehyde

((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-thiazol-2-yl-methanone

Downstream raw materials:

(1S,2R)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-thiazol-2-yl-ethanol

(1R,2R)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-thiazol-2-yl-ethanol

2-[(1R,2S)-1,2-Bis-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-thiazole

Acetic acid (1R,2S)-2-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-thiazol-2-yl-ethyl ester