(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 172213-39-7
• Molecular Formula: C₄₂H₆₇NO₄Si
• Molecular Weight: 678.084
• Mol file: 172213-39-7.mol

Synonyms:

Chemical Property of (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester

There total 10 articles about (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid 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: 64.0%

(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((Z)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester (177186-44-6) → (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester (172213-39-7)

Guidance literature:

With thiophenol; In cyclohexane; Irradiation;

DOI:10.1016/0957-4166(96)00087-0

Reference yield:

(2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-butane-1,2-diol (176967-02-5) → (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester (172213-39-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 83 percent / Et₃N / H₂O; dioxane / 4.5 h / 20 °C

2: 97 percent / pyridine / CH₂Cl₂ / 96 h / 20 °C

3: 87 percent / BF₃*Et₂O / acetone / 120 h / 20 °C

4: 95 percent / K₂CO₃ / tetrahydrofuran; H₂O / 24 h / 20 °C

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -65 deg C, 45 min, 2.) CH₂Cl₂, 1.5 h

6: 1.) n-butyllithium / 1.) THF, -78 deg C, THF, 2.) THF, 20 deg C, 3 d

7: 64 percent / phenylsulfide / cyclohexane / Irradiation

With pyridine; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; thiophenol; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; cyclohexane; water; acetone;

DOI:10.1016/0957-4166(96)00087-0

Reference yield:

(2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane (177186-42-4) → (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester (172213-39-7)

Guidance literature:

Multi-step reaction with 8 steps

1: aq. trifluoroacetic acid / 5 h / -5 °C

2: 83 percent / Et₃N / H₂O; dioxane / 4.5 h / 20 °C

3: 97 percent / pyridine / CH₂Cl₂ / 96 h / 20 °C

4: 87 percent / BF₃*Et₂O / acetone / 120 h / 20 °C

5: 95 percent / K₂CO₃ / tetrahydrofuran; H₂O / 24 h / 20 °C

6: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -65 deg C, 45 min, 2.) CH₂Cl₂, 1.5 h

7: 1.) n-butyllithium / 1.) THF, -78 deg C, THF, 2.) THF, 20 deg C, 3 d

8: 64 percent / phenylsulfide / cyclohexane / Irradiation

With pyridine; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; thiophenol; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; cyclohexane; water; acetone;

DOI:10.1016/0957-4166(96)00087-0

upstream raw materials:

(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-((Z)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

3-<(tert-Butoxycarbonyl)amino>-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-N,2-O-isopropylidene-D-threose

(2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-butane-1,2-diol