2-O-benzyl-1-(2-thiazolyl)-2,3-butanediol

Base Information

• Chemical Name: 2-O-benzyl-1-(2-thiazolyl)-2,3-butanediol
• CAS No.: 118377-26-7
• Molecular Formula: C₁₄H₁₇NO₂S
• Molecular Weight: 263.36
• Mol file: 118377-26-7.mol

Synonyms:2-O-benzyl-1-(2-thiazolyl)-2,3-butanediol

Chemical Property of 2-O-benzyl-1-(2-thiazolyl)-2,3-butanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-benzyl-1-(2-thiazolyl)-2,3-butanediol

There total 11 articles about 2-O-benzyl-1-(2-thiazolyl)-2,3-butanediol 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: 60.0%

2,4,6-Trimethyl-benzenesulfonic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-thiazol-2-yl-butyl ester (118397-61-8) → 2-O-benzyl-1-(2-thiazolyl)-2,3-butanediol (118377-26-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00264a035

Reference yield:

benzyl bromide (100-39-0) → 2-O-benzyl-1-(2-thiazolyl)-2,3-butanediol (118377-26-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) 50percent NaH, 2.) tetra-n-butylammonium iodide / 1.) reflux, 20 min, 2.) room temp., overnight

2: 94 percent / acetonitrile / 7 h / Heating

3: 70 percent / NaBH₄ / methanol / 0.5 h / -10 °C

4: 86 percent / H₂O, HgCl₂ / acetonitrile / 0.25 h / Ambient temperature

5: CH₂Cl₂ / 12 h / Ambient temperature

6: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

7: 5 h / Heating

8: Bu₃SnH / toluene / 6 h / Heating

9: CF₃COOH / H₂O / 0 °C

10: pyridine / 12 h / Ambient temperature

11: 60 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; mercury dichloride; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo00264a035

Reference yield:

(R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (103795-12-6) → 2-O-benzyl-1-(2-thiazolyl)-2,3-butanediol (118377-26-7)

Guidance literature:

Multi-step reaction with 7 steps

1: CH₂Cl₂ / 12 h / Ambient temperature

2: tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

3: 5 h / Heating

4: Bu₃SnH / toluene / 6 h / Heating

5: CF₃COOH / H₂O / 0 °C

6: pyridine / 12 h / Ambient temperature

7: 60 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/jo00264a035

upstream raw materials:

2,4,6-Trimethyl-benzenesulfonic acid (2R,3S)-3-benzyloxy-2-hydroxy-4-thiazol-2-yl-butyl ester

benzyl bromide

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

(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol