tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate

Base Information

• Chemical Name: tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate
• CAS No.: 117997-58-7
• Molecular Formula: C₁₈H₃₁NO₄
• Molecular Weight: 325.448
• Mol file: 117997-58-7.mol

Synonyms:tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate

Chemical Property of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate

There total 28 articles about tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate 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: 95.0%

(4S-trans)-4-(cyclohexylmethyl)-5-[[(methoxy)methylamino]carbonyl]-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester (138448-17-6) → tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (117997-58-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/S0040-4039(00)91634-4

Reference yield:

(4S,5R)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-methanol (143122-12-7) → tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (117997-58-7)

Guidance literature:

With oxalyl dichloride; triethylamine; In dimethyl sulfoxide; at -65 ℃; for 1h; Yield given;

DOI:10.1016/S0040-4039(97)10677-3

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (117997-58-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / H₂ / PtO₂ / ethanol

2: 95 percent / 1,1'-carbonyldiimidazole, Et₃N / tetrahydrofuran

3: 93 percent / LiAlH₄ / diethyl ether

4: 1) n-BuLi, 2) ZnBr₂ / 1) THF, 2) THF

5: 78 percent / PpTSA / CH₂Cl₂

6: 80 percent / RuCl₃*H₂O, NaIO₄ / acetonitrile; CCl₄; H₂O

7: 80 percent / 1,1'-carbonyldiimidazole, Et₃N / tetrahydrofuran

8: 95 percent / LiAlH₄ / diethyl ether

With ruthenium trichloride; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; hydrogen; pyridinium p-toluenesulfonate; triethylamine; 1,1'-carbonyldiimidazole; zinc dibromide; platinum(IV) oxide; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)91634-4

upstream raw materials:

3-<(tert-butyloxy)carbonyl>-4-(cyclohexylmethyl)-2,2-dimethyl-5-vinyloxazolidine

(4S,5S)-3-tert-butoxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-5-vinyloxazolidine

(4S-trans)-4-(cyclohexylmethyl)-5-[[(methoxy)methylamino]carbonyl]-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester

2-<(4S,5R)-3-tert-butoxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidin-5-yl>-1,3-thiazole

Downstream raw materials:

(5S,4'S,5'R)-5-<3'-<(tert-butyloxy)carbonyl>-4'-(cyclohexylmethyl)-2',2'-dimethyloxazolidin-5'-yl>-3-methylenedihydrofuran-2(4H)-one

(4S,5R)-4-Cyclohexylmethyl-5-((R)-hydroxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5S)-4-Cyclohexylmethyl-5-[(1R,2R)-1-hydroxy-2-((R)-4-methoxycarbonyl-2-thioxo-thiazolidine-3-carbonyl)-3-methyl-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

3-(3(R)-(3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(R)-oxazolidinyl)-3-hydroxy-2(R)-isopropyl-1-oxopropyl)-4(S)-(methoxycarbonyl)-1,3-thiazolidine-2-thione

Refernces

• 1、 Dondoni, Alessandro,Perrone, Daniela,Rinaldi, Marilisa. "Grignard addition to aldonitrones. Stereochemical aspects and application to the synthesis of C2-symmetric diamino alcohols and diamino diols". . p. 9252 - 9264. Retrieved 2007/10/03.
• 2、 -. "Amino acid derivatives having renin inhibiting activity". . . Retrieved 2008/06/13.