(3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-[3'-(tert-butyldimethylsilanyloxy)propylamino]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-[3'-(tert-butyldimethylsilanyloxy)propylamino]propionic acid methyl ester
• CAS No.: 566202-98-0
• Molecular Formula: C₆₀H₈₀N₂O₉Si₂
• Molecular Weight: 1029.47

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

Chemical Property:

Purity/Quality:

Safty Information:

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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-[3'-(tert-butyldimethylsilanyloxy)propylamino]propionic acid methyl ester

There total 27 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-[3'-(tert-butyldimethylsilanyloxy)propylamino]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: 93.0%

(3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-(2''-nitrobenzenesulfonyl-[3'-(tert-butyldimethylsilanyloxy)propyl]amino)propionic acid methyl ester (566202-97-9) → (3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-[3'-(tert-butyldimethylsilanyloxy)propylamino]propionic acid methyl ester (566202-98-0)

Guidance literature:

With potassium hydroxide; thiophenol; In acetonitrile; at 60 ℃; for 2h;

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-[3'-(tert-butyldimethylsilanyloxy)propylamino]propionic acid methyl ester (566202-98-0)

Guidance literature:

Multi-step reaction with 12 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

11: 95 percent / diethyl azodicarboxylate; PPh₃ / toluene / 1 h / 60 °C

12: 93 percent / PhSH; aq. KOH / acetonitrile / 2 h / 60 °C

With pyridine; tetrachloromethane; palladium diacetate; potassium hydroxide; 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 / 11: 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-[3'-(tert-butyldimethylsilanyloxy)propylamino]propionic acid methyl ester (566202-98-0)

Guidance literature:

Multi-step reaction with 12 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

11: 95 percent / diethyl azodicarboxylate; PPh₃ / toluene / 1 h / 60 °C

12: 93 percent / PhSH; aq. KOH / acetonitrile / 2 h / 60 °C

With pyridine; tetrachloromethane; palladium diacetate; potassium hydroxide; 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 / 11: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.06.144

upstream raw materials:

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

p-benzyloxybenzaldehyde

4-benzyloxybenzyl alcohol

4-hydroxy-benzaldehyde

Downstream raw materials:

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

(-)-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

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