allyl (2R,3S)-2-(((S)-N-(4-bromobenzyl)-2-(4-fluorobenzamido)-3-methylbutanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate

Base Information

• Chemical Name: allyl (2R,3S)-2-(((S)-N-(4-bromobenzyl)-2-(4-fluorobenzamido)-3-methylbutanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate
• CAS No.: 1592908-69-4
• Molecular Formula: C₃₆H₄₁BrFN₃O₈
• Molecular Weight: 742.639

Synonyms:allyl (2R,3S)-2-(((S)-N-(4-bromobenzyl)-2-(4-fluorobenzamido)-3-methylbutanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate

Chemical Property of allyl (2R,3S)-2-(((S)-N-(4-bromobenzyl)-2-(4-fluorobenzamido)-3-methylbutanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate

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Technology Process of allyl (2R,3S)-2-(((S)-N-(4-bromobenzyl)-2-(4-fluorobenzamido)-3-methylbutanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate

There total 6 articles about allyl (2R,3S)-2-(((S)-N-(4-bromobenzyl)-2-(4-fluorobenzamido)-3-methylbutanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate 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: 60.0%

allyl (2R,3S)-2-((4-bromobenzylamino)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate (1592908-64-9) + (S)-2-(4-fluoro-benzoylamino)-3-methyl-butyric acid → allyl (2R,3S)-2-(((S)-N-(4-bromobenzyl)-2-(4-fluorobenzamido)-3-methylbutanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate (1592908-69-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; PyBroP; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201301769

Reference yield:

allyl (2R,3S)-2-(azidomethyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate → allyl (2R,3S)-2-(((S)-N-(4-bromobenzyl)-2-(4-fluorobenzamido)-3-methylbutanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate (1592908-69-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triphenylphosphine / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

2: sodium cyanoborohydride; acetic acid / ethanol / 4 h / 20 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine; PyBroP / dichloromethane / 20 °C / Inert atmosphere

With sodium cyanoborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; PyBroP; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1002/ejoc.201301769

Reference yield:

allyl (2R,3S)-2-(aminomethyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate → allyl (2R,3S)-2-(((S)-N-(4-bromobenzyl)-2-(4-fluorobenzamido)-3-methylbutanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate (1592908-69-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium cyanoborohydride; acetic acid / ethanol / 4 h / 20 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine; PyBroP / dichloromethane / 20 °C / Inert atmosphere

With sodium cyanoborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; PyBroP; In ethanol; dichloromethane;

DOI:10.1002/ejoc.201301769

upstream raw materials:

allyl (2R,3S)-2-((4-bromobenzylamino)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate

(2S,3S)-ethyl-3-(allyloxycarbonylamino)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-2-carboxylate

C₁₅H₂₁NO₆

Downstream raw materials:

C₃₂H₃₇BrFN₃O₆

N-((S)-1-((((2R,3S)-3-benzamido-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-2-yl)methyl)(4-bromobenzyl)amino)-3-methyl-1-oxobutan-2-yl)-4-fluorobenzamide

(7S,10aR,15bS)-1-benzoyl-9-(4-bromobenzyl)-6-(4-fluorobenzoyl)-7-isopropyl-13-((2-methoxyethoxy)methoxy)-1,2,6,7,9,10,10a,15b-octahydrobenzofuro[2,3-f][1,4,8]triazacyclododecin-8(5H)-one

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