2-((1R,2S)-2-Benzyloxy-1-hydroxy-3-methyl-butyl)-malonic acid di-tert-butyl ester

Base Information

• Chemical Name: 2-((1R,2S)-2-Benzyloxy-1-hydroxy-3-methyl-butyl)-malonic acid di-tert-butyl ester
• CAS No.: 217181-98-1
• Molecular Formula: C₂₃H₃₆O₆
• Molecular Weight: 408.535
• Mol file: 217181-98-1.mol

Synonyms:2-((1R,2S)-2-Benzyloxy-1-hydroxy-3-methyl-butyl)-malonic acid di-tert-butyl ester

Chemical Property of 2-((1R,2S)-2-Benzyloxy-1-hydroxy-3-methyl-butyl)-malonic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1R,2S)-2-Benzyloxy-1-hydroxy-3-methyl-butyl)-malonic acid di-tert-butyl ester

There total 1 articles about 2-((1R,2S)-2-Benzyloxy-1-hydroxy-3-methyl-butyl)-malonic acid di-tert-butyl ester 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:

(S)-(+)-2-(benzyloxy)-3-methylbutanal (110840-39-6) + C11H19LiO4 → 2-((1S,2S)-2-Benzyloxy-1-hydroxy-3-methyl-butyl)-malonic acid di-tert-butyl ester + 2-((1R,2S)-2-Benzyloxy-1-hydroxy-3-methyl-butyl)-malonic acid di-tert-butyl ester (217181-98-1)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; at -78 ℃; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(99)00041-5

Reference yield: 70.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 2-((1R,2S)-2-Benzyloxy-1-hydroxy-3-methyl-butyl)-malonic acid di-tert-butyl ester (217181-98-1) → 2-((1R,2S)-2-Benzyloxy-3-methyl-1-trimethylsilanyloxy-butyl)-malonic acid di-tert-butyl ester (228863-34-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0957-4166(99)00041-5

Reference yield:

2-((1R,2S)-2-Benzyloxy-1-hydroxy-3-methyl-butyl)-malonic acid di-tert-butyl ester (217181-98-1) → (1R,4R,5R)-4-Hydroxy-4-isopropyl-1-[(E)-(3-phenyl-acryloyl)]-6-oxa-3-aza-bicyclo[3.1.0]hexan-2-one

Guidance literature:

Multi-step reaction with 11 steps

1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 1.) lithium hexamethyldisilazide, 2.) I₂ / 1.) THF, -46 deg C to RT, 2.) THF, -46 deg C

3: tetrabutylammonium fluoride / tetrahydrofuran / -46 - 20 °C

4: 93 percent / H₂ / Pd(OH)2 / methanol / 50 °C

5: HCOOH / Ambient temperature

6: (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, i-Pr₂EtN / CH₂Cl₂ / 0 °C

7: NH₃ / methanol / Ambient temperature

8: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

9: 80 percent / t-BuLi / tetrahydrofuran / -78 °C

10: 82 percent / triethylamine trihydrofluoride / dimethylformamide / Ambient temperature

11: 1.) Dess-Martin reagent, 2.) SiO₂ / 1.) CH₂Cl₂, RT, 2.) CH₂Cl₂, RT

With 2,6-dimethylpyridine; formic acid; triethylamine trihydrofluoride; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonia; hydrogen; iodine; tert.-butyl lithium; silica gel; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(99)00041-5

upstream raw materials:

(S)-(+)-2-(benzyloxy)-3-methylbutanal

Downstream raw materials:

2-((1R,2S)-2-Benzyloxy-3-methyl-1-trimethylsilanyloxy-butyl)-malonic acid di-tert-butyl ester

(2R,3S)-3-((S)-1-Hydroxy-2-methyl-propyl)-2-[(E)-(3-phenyl-acryloyl)]-oxirane-2-carboxylic acid amide

(S)-3-((S)-1-Benzyloxy-2-methyl-propyl)-oxirane-2,2-dicarboxylic acid di-tert-butyl ester

(2R,3S)-3-((S)-2-Methyl-1-trimethylsilanyloxy-propyl)-2-[(E)-(3-phenyl-acryloyl)]-oxirane-2-carboxylic acid amide