(2S,2′S)-dimethyl 3,3′-(4,8-dibromodibenzo[d,f ][1,3]dioxepine-2,10-diyl)bis(2-(benzyloxycarbonylamino)propanoate)

Base Information

• Chemical Name: (2S,2′S)-dimethyl 3,3′-(4,8-dibromodibenzo[d,f ][1,3]dioxepine-2,10-diyl)bis(2-(benzyloxycarbonylamino)propanoate)
• CAS No.: 1394296-02-6
• Molecular Formula: C₃₇H₃₄Br₂N₂O₁₀
• Molecular Weight: 826.492

Synonyms:(2S,2′S)-dimethyl 3,3′-(4,8-dibromodibenzo[d,f ][1,3]dioxepine-2,10-diyl)bis(2-(benzyloxycarbonylamino)propanoate)

Chemical Property of (2S,2′S)-dimethyl 3,3′-(4,8-dibromodibenzo[d,f ][1,3]dioxepine-2,10-diyl)bis(2-(benzyloxycarbonylamino)propanoate)

Chemical Property:

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Technology Process of (2S,2′S)-dimethyl 3,3′-(4,8-dibromodibenzo[d,f ][1,3]dioxepine-2,10-diyl)bis(2-(benzyloxycarbonylamino)propanoate)

There total 2 articles about (2S,2′S)-dimethyl 3,3′-(4,8-dibromodibenzo[d,f ][1,3]dioxepine-2,10-diyl)bis(2-(benzyloxycarbonylamino)propanoate) 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: 26.0%

diiodomethane (75-11-6) + (2S,2′S)-dimethyl 3,3′-(5,5′-dibromo-6,6′-dihydroxybiphenyl-3,3′-diyl)bis(2-(benzyloxycarbonylamino)propanoate) (1394296-00-4) → (2S,2′S)-dimethyl 3,3′-(4,8-dibromodibenzo[d,f ][1,3]dioxepine-2,10-diyl)bis(2-(benzyloxycarbonylamino)propanoate) (1394296-02-6)

Guidance literature:

(2S,2′S)-dimethyl 3,3′-(5,5′-dibromo-6,6′-dihydroxybiphenyl-3,3′-diyl)bis(2-(benzyloxycarbonylamino)propanoate); With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;

diiodomethane; at 50 ℃; for 29h;

DOI:10.1039/c2ob25874a

Reference yield:

N-(benzyloxycarbonyl)-L-tyrosine methyl ester (13512-31-7) → (2S,2′S)-dimethyl 3,3′-(4,8-dibromodibenzo[d,f ][1,3]dioxepine-2,10-diyl)bis(2-(benzyloxycarbonylamino)propanoate) (1394296-02-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid; thallium(III) trifluoroacetate; vanadium(V) oxytrifluoride / dichloromethane; ethyl acetate / 0.75 h / -20 °C / Inert atmosphere

2.1: N-Bromosuccinimide / acetonitrile / 0.25 h / 0 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

3.2: 29 h / 50 °C

With N-Bromosuccinimide; vanadium(V) oxytrifluoride; sodium hydride; trifluoroacetic acid; thallium(III) trifluoroacetate; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c2ob25874a

Reference yield: 100.0%

(2S,2′S)-dimethyl 3,3′-(4,8-dibromodibenzo[d,f ][1,3]dioxepine-2,10-diyl)bis(2-(benzyloxycarbonylamino)propanoate) (1394296-02-6) → (2S,2′S)-3,3′-(4,8-dibromodibenzo[d,f][1,3]dioxepine-2,10-diyl)-bis(2-(benzyloxycarbonylamino)propanoic acid) (1394296-04-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1039/c2ob25874a

upstream raw materials:

N-(benzyloxycarbonyl)-L-tyrosine methyl ester

diiodomethane

(2S,2′S)-dimethyl 3,3′-(5,5′-dibromo-6,6′-dihydroxybiphenyl-3,3′-diyl)bis(2-(benzyloxycarbonylamino)propanoate)

Downstream raw materials:

(2S,2′S)-3,3′-(4,8-dibromodibenzo[d,f][1,3]dioxepine-2,10-diyl)-bis(2-(benzyloxycarbonylamino)propanoic acid)

benzyl (2S,2′S)-3,3′-(4,8-dibromodibenzo[d,f][1,3]dioxepine-2,10-diyl)bis(1-(3-bromo-4-hydroxyphenethylamino)-1-oxopropane-3,2-diyl)dicarbamate

(2S,2′S)-3,3′-(4,8-dibromodibenzo[d,f][1,3]dioxepine-2,10-diyl)-bis(2-amino-N-(3-bromo-4-hydroxyphenethyl)propanamide)

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