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

Base Information

• Chemical Name: 2-[(1S,2S)-1,2-Bis-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-thiazole
• CAS No.: 142760-44-9
• Molecular Formula: C₂₄H₂₇NO₄S
• Molecular Weight: 425.549
• Mol file: 142760-44-9.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 2-[(1S,2S)-1,2-Bis-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-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:

benzyl bromide (100-39-0) → 2-[(1S,2S)-1,2-Bis-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-thiazole (142760-44-9)

Guidance literature:

Multi-step reaction with 7 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

7: 1.) LiAlH₄, 2a.) NaH, 2b.) Bu₄NI / 1.) Et₂O, -78 deg C, 2 h, 2a.) THF, reflux, 20 min, 2b.) r. t., 14 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; 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) → 2-[(1S,2S)-1,2-Bis-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-thiazole (142760-44-9)

Guidance literature:

Multi-step reaction with 8 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

8: 1.) LiAlH₄, 2a.) NaH, 2b.) Bu₄NI / 1.) Et₂O, -78 deg C, 2 h, 2a.) THF, reflux, 20 min, 2b.) r. t., 14 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; 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

Reference yield:

(1S,2R)-2,3-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol (104470-54-4) → 2-[(1S,2S)-1,2-Bis-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-thiazole (142760-44-9)

Guidance literature:

Multi-step reaction with 7 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

7: 1.) LiAlH₄, 2a.) NaH, 2b.) Bu₄NI / 1.) Et₂O, -78 deg C, 2 h, 2a.) THF, reflux, 20 min, 2b.) r. t., 14 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; 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

upstream raw materials:

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

(1S,2R)-2,3-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol

Downstream raw materials:

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