(3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-(2-nitrobenzenesulfonylamino)propionic acid methyl ester

Base Information

• Chemical Name: (3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-(2-nitrobenzenesulfonylamino)propionic acid methyl ester
• CAS No.: 566202-81-1
• Molecular Formula: C₅₇H₆₃N₃O₁₂SSi
• Molecular Weight: 1042.29

Synonyms:(3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-(2-nitrobenzenesulfonylamino)propionic acid methyl ester

Chemical Property of (3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-(2-nitrobenzenesulfonylamino)propionic acid methyl ester

Chemical Property:

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Technology Process of (3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-(2-nitrobenzenesulfonylamino)propionic acid methyl ester

There total 25 articles about (3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-(2-nitrobenzenesulfonylamino)propionic acid methyl 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: 72.0%

2-Nitrobenzenesulfonyl chloride (1694-92-4) + (3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-aminopropionic acid methyl ester (566202-96-8) → (3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-(2-nitrobenzenesulfonylamino)propionic acid methyl ester (566202-81-1)

Guidance literature:

With sodium carbonate; In dichloromethane; for 4h;

DOI:10.1021/ja036011k DOI:10.1016/j.tet.2004.06.144

Reference yield:

(2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid (566202-75-3) → (3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-(2-nitrobenzenesulfonylamino)propionic acid methyl ester (566202-81-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran; toluene / 0 - 20 °C

2: 88 percent / PhSH; K₂CO₃ / dimethylformamide; acetonitrile / 0.67 h / 50 °C

3: 67 percent / Me₂AlCl / CH₂Cl₂ / 3 h / Heating

4: 88 percent / pyridine / 0 - 20 °C

5: 84 percent / Pd(OAc)2; tris(o-tolyl)phosphine / dimethylformamide / 24 h / 100 °C

6: 66 percent / (DHQD)2PHAL; K₂OsO₂(OH)4 / propan-1-ol; H₂O / 4 h / 20 °C

7: 87 percent / CCl₄; PPh₃ / toluene / 2 h / 100 °C

8: ammonium formate / Pd/C / methanol / 1.25 h / 60 °C

9: 118 mg / diethyl azodicarboxylate; PPh₃ / toluene / 2 h / 60 °C

10: 72 percent / aq. Na₂CO₃ / CH₂Cl₂ / 4 h

With pyridine; tetrachloromethane; palladium diacetate; potassium dioxotetrahydroxoosmate(VI); ammonium formate; dimethylaluminum chloride; sodium carbonate; potassium carbonate; thiophenol; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Mitsunobu reaction / 5: Heck reaction / 6: Sharpless aminohydroxylation / 9: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.06.144

Reference yield:

N-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-N-(3-hydroxy-propyl)-2-nitro-benzenesulfonamide (566202-76-4) → (3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-(2-nitrobenzenesulfonylamino)propionic acid methyl ester (566202-81-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran; toluene / 0 - 20 °C

2: 88 percent / PhSH; K₂CO₃ / dimethylformamide; acetonitrile / 0.67 h / 50 °C

3: 67 percent / Me₂AlCl / CH₂Cl₂ / 3 h / Heating

4: 88 percent / pyridine / 0 - 20 °C

5: 84 percent / Pd(OAc)2; tris(o-tolyl)phosphine / dimethylformamide / 24 h / 100 °C

6: 66 percent / (DHQD)2PHAL; K₂OsO₂(OH)4 / propan-1-ol; H₂O / 4 h / 20 °C

7: 87 percent / CCl₄; PPh₃ / toluene / 2 h / 100 °C

8: ammonium formate / Pd/C / methanol / 1.25 h / 60 °C

9: 118 mg / diethyl azodicarboxylate; PPh₃ / toluene / 2 h / 60 °C

10: 72 percent / aq. Na₂CO₃ / CH₂Cl₂ / 4 h

With pyridine; tetrachloromethane; palladium diacetate; potassium dioxotetrahydroxoosmate(VI); ammonium formate; dimethylaluminum chloride; sodium carbonate; potassium carbonate; thiophenol; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Mitsunobu reaction / 5: Heck reaction / 6: Sharpless aminohydroxylation / 9: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.06.144

upstream raw materials:

2-Nitrobenzenesulfonyl chloride

(3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-aminopropionic acid methyl ester

p-benzyloxybenzaldehyde

4-benzyloxybenzyl alcohol

Downstream raw materials:

(-)-ephedradine A

O-benzyloxy-N₁-benzyloxycarbonyl-ephedradine A

19-(4-benzyloxyphenyl)-3-(3-hydroxypropyl)-13-methoxycarbonylmethyl-8-(2-nitrobenzenesulfonyl)-2-oxo-18-oxa-3,8,12-triazatricyclo[12.5.2.0^0.0]heneicosa-14⁽²¹⁾,15,17⁽²⁰⁾-triene-12-carboxylic acid benzyl ester

O-benzyloxy-N₁-benzyloxycarbonyl-N₂-nitrobenzenesulfonyl-ephedradine A

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