L-Phenylalanine, (2R)-2-(3,5-dichloro-4-methoxyphenyl)-N-[(1,1-dimethylethoxy)carbonyl] glycyl-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester

Base Information

Chemical Name:L-Phenylalanine, (2R)-2-(3,5-dichloro-4-methoxyphenyl)-N-[(1,1-dimethylethoxy)carbonyl] glycyl-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester
CAS No.:586413-49-2
Molecular Formula:C31H41BCl2N2O8
Molecular Weight:651.392
Hs Code.:

L-Phenylalanine,
(2R)-2-(3,5-dichloro-4-methoxyphenyl)-N-[(1,1-dimethylethoxy)carbonyl]
glycyl-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl
ester

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Chemical Property of L-Phenylalanine, (2R)-2-(3,5-dichloro-4-methoxyphenyl)-N-[(1,1-dimethylethoxy)carbonyl] glycyl-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester

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Technology Process of L-Phenylalanine, (2R)-2-(3,5-dichloro-4-methoxyphenyl)-N-[(1,1-dimethylethoxy)carbonyl] glycyl-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester

There total 1 articles about L-Phenylalanine, (2R)-2-(3,5-dichloro-4-methoxyphenyl)-N-[(1,1-dimethylethoxy)carbonyl] glycyl-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 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: 99.0%

: 586413-67-4
(S)-2-{[(R)-2-tert-Butoxycarbonylamino-2-(3,5-dichloro-4-hydroxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester

: 18107-18-1
diazomethyl-trimethyl-silane

: 586413-49-2
(S)-2-{[(R)-2-tert-Butoxycarbonylamino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester

Guidance literature:: In methanol; hexane; dichloromethane; at 22 ℃; for 1.5h;
DOI:10.1021/ja030249r

Reference yield:

: 586413-49-2
(S)-2-{[(R)-2-tert-Butoxycarbonylamino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester

: (S)-2-{[(R)-2-Amino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester; hydrochloride

Guidance literature:: With hydrogenchloride; In methanol; at -78 - 22 ℃;
DOI:10.1021/ja030249r

Reference yield:

: 586413-49-2
(S)-2-{[(R)-2-tert-Butoxycarbonylamino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester

: 586413-69-6
(8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: HCl / methanol / -78 - 22 °C

2: 3.11 g / NaHCO₃; 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide / tetrahydrofuran; dimethylformamide / 12 h / 22 °C

3: NH₄OAc; aq. NaIO₄ / acetone / 12 h / 22 °C

4: 650 mg / Cu(OAc)2; 4A molecular sieves; Et₃N / CH₂Cl₂; methanol / 6 h / 22 °C

5: 98 percent / HCl / methanol / 1.5 h / 22 °C

6: 860 mg / 2,6-lutidine / CH₂Cl₂ / 2 h

With 2,6-dimethylpyridine; hydrogenchloride; sodium periodate; 1-hydroxy-7-aza-benzotriazole; copper diacetate; 4 A molecular sieve; ammonium acetate; sodium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja030249r