Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester
• CAS No.: 215313-29-4
• Molecular Formula: C₆₇H₁₁₉N₃O₁₁S
• Molecular Weight: 1174.76

Synonyms:

Chemical Property of Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester

Chemical Property:

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Safty Information:

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Technology Process of Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester

There total 5 articles about Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl 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:

n-dodecanoyl chloride (112-16-3) → Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester (215313-29-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / DMAP / pyridine; pentane / 40 h / Ambient temperature

2: 77 percent / CF₃SO₃SiMe₃ / CH₂Cl₂ / 48 h

3: 94 percent / Et₂NH / CH₂Cl₂ / 3 h

4: NaCNBH₃ / acetonitrile; tetrahydrofuran / 73 h

With dmap; trimethylsilyl trifluoromethanesulfonate; sodium cyanoborohydride; diethylamine; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile; pentane;

DOI:10.1016/S0968-0896(98)00087-X

Reference yield:

D-Galactose (10257-28-0) → Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester (215313-29-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / DMAP / pyridine; pentane / 40 h / Ambient temperature

2: 77 percent / CF₃SO₃SiMe₃ / CH₂Cl₂ / 48 h

3: 94 percent / Et₂NH / CH₂Cl₂ / 3 h

4: NaCNBH₃ / acetonitrile; tetrahydrofuran / 73 h

With dmap; trimethylsilyl trifluoromethanesulfonate; sodium cyanoborohydride; diethylamine; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile; pentane;

DOI:10.1016/S0968-0896(98)00087-X

Reference yield:

1-S-acetyl-2,3,4,6-tetra-O-lauroyl-1-thio-β-D-galactopyranose (207907-62-8) → Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester (215313-29-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Et₂NH / CH₂Cl₂ / 3 h

2: NaCNBH₃ / acetonitrile; tetrahydrofuran / 73 h

With sodium cyanoborohydride; diethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/S0968-0896(98)00087-X

upstream raw materials:

histidine methyl ester hydrochloride

cyclohexan-2-on-1-yl 2,3,4,6-tetra-O-lauroyl-1-thio-β-D-galactopyranoside

n-dodecanoyl chloride

D-Galactose

Downstream raw materials:

(S)-3-(1H-Imidazol-4-yl)-2-[2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cyclohexylamino]-propionic acid methyl ester

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