2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester
• CAS No.: 81689-26-1
• Molecular Formula: C₂₉H₃₉N₃O₉
• Molecular Weight: 573.643

Synonyms:2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester

There total 6 articles about 2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl 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: 90.4%

(2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester (81658-13-1) → 2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester (81689-26-1)

Guidance literature:

With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; ethanol; for 2.4h; Ambient temperature;

DOI:10.1016/S0040-4039(00)87057-4

Reference yield:

N-benzyloxycarbonyl-O-t-butyl-L-serine (1676-75-1) → 2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester (81689-26-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 62 percent / diphenyl phosphorazidate, K₂CO₃ sesquihydrate / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temp., 14 h

2: trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

3: 67 percent / 4-N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: 1.) HCl, 2.) NaHCO₃, NaBH₄ / 1.) MeOH, 40 deg C, 2.5 h; 2.) EtOH, -10 deg C, 1 h

5: 76.5 percent / diethyl phosphorocyanidate, Et₃N

6: 90.4 percent / LiCl-NaBH₄ / ethanol; tetrahydrofuran / 2.4 h / Ambient temperature

With hydrogenchloride; dmap; sodium tetrahydroborate; diethyl cyanophosphonate; diphenyl phosphoryl azide; sodium hydrogencarbonate; potassium carbonate; triethylamine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)87057-4

Reference yield:

5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester (81658-10-8) → 2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester (81689-26-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / 4-N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) HCl, 2.) NaHCO₃, NaBH₄ / 1.) MeOH, 40 deg C, 2.5 h; 2.) EtOH, -10 deg C, 1 h

3: 76.5 percent / diethyl phosphorocyanidate, Et₃N

4: 90.4 percent / LiCl-NaBH₄ / ethanol; tetrahydrofuran / 2.4 h / Ambient temperature

With hydrogenchloride; dmap; sodium tetrahydroborate; diethyl cyanophosphonate; sodium hydrogencarbonate; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)87057-4

upstream raw materials:

(2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester

N-benzyloxycarbonyl-O-t-butyl-L-serine

5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester

5-((S)-1-Benzyloxycarbonylamino-2-tert-butoxy-ethyl)-oxazole-4-carboxylic acid methyl ester

Downstream raw materials:

{(S)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-hydroxy-ethyl}-carbamic acid benzyl ester

{(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl ester

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 81689-26-1 2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send