N-<<(benzyloxy)carbonyl>methyl>-N-(3-hydroxypropyl)-(R)-3-(benzyloxy)tetradecanamide

Base Information

• Chemical Name: N-<<(benzyloxy)carbonyl>methyl>-N-(3-hydroxypropyl)-(R)-3-(benzyloxy)tetradecanamide
• CAS No.: 142981-92-8
• Molecular Formula: C₃₃H₄₉NO₅
• Molecular Weight: 539.756

Synonyms:N-<<(benzyloxy)carbonyl>methyl>-N-(3-hydroxypropyl)-(R)-3-(benzyloxy)tetradecanamide

Chemical Property of N-<<(benzyloxy)carbonyl>methyl>-N-(3-hydroxypropyl)-(R)-3-(benzyloxy)tetradecanamide

Chemical Property:

Purity/Quality:

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Technology Process of N-<<(benzyloxy)carbonyl>methyl>-N-(3-hydroxypropyl)-(R)-3-(benzyloxy)tetradecanamide

There total 2 articles about N-<<(benzyloxy)carbonyl>methyl>-N-(3-hydroxypropyl)-(R)-3-(benzyloxy)tetradecanamide 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: 30.0%

N-((R)-3-Benzyloxytetradecanoyloxy)succinimid (101649-06-3) + benzyl 2-<(3-hydroxypropyl)amino>acetate (142982-11-4) → N-<<(benzyloxy)carbonyl>methyl>-N-(3-hydroxypropyl)-(R)-3-(benzyloxy)tetradecanamide (142981-92-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1021/jm00097a003

Reference yield:

Benzyl bromoacetate (5437-45-6) → N-<<(benzyloxy)carbonyl>methyl>-N-(3-hydroxypropyl)-(R)-3-(benzyloxy)tetradecanamide (142981-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 36 percent / CH₂Cl₂ / 4 h / -60 - 20 °C

2: 30 percent / N-ethyldiisopropylamine / dimethylformamide / 24 h / Ambient temperature

With N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00097a003

Reference yield: 22.0%

N-<<(benzyloxy)carbonyl>methyl>-N-(3-hydroxypropyl)-(R)-3-(benzyloxy)tetradecanamide (142981-92-8) + 1,3,4,6-tetra-O-acetyl-2-amino-2-N-<(R)-3-(benzyloxy)tetrdecanoyl>-2-deoxy-β-D-glucopyranose (142981-91-7) → 3-methyl>-N-<(R)-3-(benzyloxy)tetradecanoyl>amino>propyl 3,4,6-tri-O-acetyl-2-amino-2-N-<(R)-3-(benzyloxy)tetrdecanoyl>-2-deoxy-β-D-glucopyranoside (142981-93-9)

Guidance literature:

With calcium sulfate; iron(III) chloride; In dichloromethane; for 44h;

DOI:10.1021/jm00097a003

upstream raw materials:

N-((R)-3-Benzyloxytetradecanoyloxy)succinimid

benzyl 2-<(3-hydroxypropyl)amino>acetate

Benzyl bromoacetate

Downstream raw materials:

3-methyl>-N-<(R)-3-(benzyloxy)tetradecanoyl>amino>propyl 3,4,6-tri-O-acetyl-2-amino-2-N-<(R)-3-(benzyloxy)tetrdecanoyl>-2-deoxy-β-D-glucopyranoside

3--N-<(methoxycarbonyl)methyl>amino>propyl 2-amino-2-N-<(R)-3-(benzyloxy)tetradecanoyl>-2-deoxy-β-D-glucopyranoside

3--N-<<(benzyloxy)carbonyl>methyl>amino>propyl 2-amino-2-N-<(R)-3-(benzyloxy)tetradecanoyl>-2-deoxy-β-D-glucopyranoside

3-methyl>-N-<(R)-3-(benzyloxy)tetradecanoyl>amino>propyl 2-amino-4,6-O-benzylidene-2-N-<(R)-3-(benzyloxy)tetrdecanoyl>-2-deoxy-β-D-glucopyranoside

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