4-Morpholinecarboxylic acid, 3-(diethoxymethyl)-2-oxo-5,6-diphenyl-, phenylmethyl ester, (3R,5R,6S)-

Base Information

• Chemical Name: 4-Morpholinecarboxylic acid, 3-(diethoxymethyl)-2-oxo-5,6-diphenyl-, phenylmethyl ester, (3R,5R,6S)-
• CAS No.: 578710-37-9
• Molecular Formula: C29H31NO6
• Molecular Weight: 489.568
• Mol file: 578710-37-9.mol

Synonyms:

Chemical Property of 4-Morpholinecarboxylic acid, 3-(diethoxymethyl)-2-oxo-5,6-diphenyl-, phenylmethyl ester, (3R,5R,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Morpholinecarboxylic acid, 3-(diethoxymethyl)-2-oxo-5,6-diphenyl-, phenylmethyl ester, (3R,5R,6S)-

There total 1 articles about 4-Morpholinecarboxylic acid, 3-(diethoxymethyl)-2-oxo-5,6-diphenyl-, phenylmethyl ester, (3R,5R,6S)- 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: 85.0%

(5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (105228-46-4,335159-14-3) + orthoformic acid triethyl ester (122-51-0) → (3R,5R,6S)-3-Diethoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (578710-37-9)

Guidance literature:

(5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one; With titanium tetrachloride; triethylamine; In dichloromethane; at -78 ℃; for 0.25h;

orthoformic acid triethyl ester; In dichloromethane; at -78 - 0 ℃; for 0.75h;

DOI:10.1021/ja0351241

Reference yield:

(3R,5R,6S)-3-Diethoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (578710-37-9) → Nα-CBz-DAPA-Nβ-(N,N'-di-Boc-β-Lys)-DEA-OEt (578710-43-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / H₂ / Pd(OH)2/C / ethanol; tetrahydrofuran / 48 h / 20 °C / 4395.76 Torr

2: 96 percent / HCl / 2.5 h / Heating

3: 91 percent / N-methylmorpholine; EDCI; HOBt / CH₂Cl₂ / 16 h / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ja0351241

Reference yield:

(3R,5R,6S)-3-Diethoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (578710-37-9) → C53H88N12O17*ClH

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / H₂ / Pd(OH)2/C / ethanol; tetrahydrofuran / 48 h / 20 °C / 4395.76 Torr

2: 96 percent / HCl / 2.5 h / Heating

3: 91 percent / N-methylmorpholine; EDCI; HOBt / CH₂Cl₂ / 16 h / 0 - 20 °C

4: 100 percent / H₂ / Pd(OH)2 / ethanol / 1 h / 760 Torr

5: 88 percent / diisopropylcarbodiimide; HOBt / tetrahydrofuran; dimethylformamide / 5 h / 0 - 20 °C

6: 87 percent / bis(trifluoroacetoxy)iodosobenzene; dimethylformamide; pyridine / acetonitrile; H₂O / 2.5 h

7: 89 percent / HOBt; EDCI / tetrahydrofuran; dimethylformamide / 5 h / 0 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; bis-[(trifluoroacetoxy)iodo]benzene; diisopropyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0351241

upstream raw materials:

(5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

orthoformic acid triethyl ester

Downstream raw materials:

N^α-CBz-DAPA-N^β-(N,N'-di-Boc-β-Lys)-DEA-OEt

Refernces