methyl <(4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-3-isopropoxycarbonyl-1,3-oxazolidin-5-yl>acetate

Base Information

• Chemical Name: methyl <(4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-3-isopropoxycarbonyl-1,3-oxazolidin-5-yl>acetate
• CAS No.: 138448-74-5
• Molecular Formula: C₁₉H₃₃NO₅
• Molecular Weight: 355.475
• Mol file: 138448-74-5.mol

Synonyms:methyl <(4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-3-isopropoxycarbonyl-1,3-oxazolidin-5-yl>acetate

Chemical Property of methyl <(4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-3-isopropoxycarbonyl-1,3-oxazolidin-5-yl>acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl <(4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-3-isopropoxycarbonyl-1,3-oxazolidin-5-yl>acetate

There total 7 articles about methyl <(4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-3-isopropoxycarbonyl-1,3-oxazolidin-5-yl>acetate 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: 91.0%

methyl (3R,4S)-5-cyclohexyl-3-hydroxy-4-(isopropoxycarbonyl)aminopentanoate (128625-50-3) + 2,2-dimethoxy-propane (77-76-9) → methyl <(4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-3-isopropoxycarbonyl-1,3-oxazolidin-5-yl>acetate (138448-74-5)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1248/cpb.39.2425

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → methyl <(4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-3-isopropoxycarbonyl-1,3-oxazolidin-5-yl>acetate (138448-74-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / thionyl chloride

2: 91 percent / triethylamine

3: 98 percent / sodium borohydride, lithium chloride / tetrahydrofuran; ethanol

4: 100 percent / H₂ / Rh-Al₂O₃ / acetic acid; methanol / 5 h / 3040 Torr / Ambient temperature

5: 78 percent / sulfur trioxide pyridine, triethylamine, dimethylsulfoxide / toluene / 0.33 h / Ambient temperature

6: TiCl₄, molecular sieves / CH₂Cl₂ / 1 h / -78 °C

7: 91 percent / p-toluenesulfonic acid / CH₂Cl₂ / 6 h / Ambient temperature

With sodium tetrahydroborate; thionyl chloride; molecular sieve; hydrogen; sulfur trioxide pyridine complex; titanium tetrachloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium chloride; rhodium on alumina; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; toluene;

DOI:10.1248/cpb.39.2425

Reference yield:

(S)-N-(isopropoxycarbonyl)phenylalaninol (124995-02-4) → methyl <(4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-3-isopropoxycarbonyl-1,3-oxazolidin-5-yl>acetate (138448-74-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / H₂ / Rh-Al₂O₃ / acetic acid; methanol / 5 h / 3040 Torr / Ambient temperature

2: 78 percent / sulfur trioxide pyridine, triethylamine, dimethylsulfoxide / toluene / 0.33 h / Ambient temperature

3: TiCl₄, molecular sieves / CH₂Cl₂ / 1 h / -78 °C

4: 91 percent / p-toluenesulfonic acid / CH₂Cl₂ / 6 h / Ambient temperature

With molecular sieve; hydrogen; sulfur trioxide pyridine complex; titanium tetrachloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; rhodium on alumina; In methanol; dichloromethane; acetic acid; toluene;

DOI:10.1248/cpb.39.2425

upstream raw materials:

methyl (3R,4S)-5-cyclohexyl-3-hydroxy-4-(isopropoxycarbonyl)aminopentanoate

2,2-dimethoxy-propane

L-phenylalanine

(S)-3-cyclohexyl-2-(isopropoxycarbonyl)aminopropanol