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

Base Information

• Chemical Name: Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{5-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-2,2-dimethyl-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester
• CAS No.: 215313-32-9
• Molecular Formula: C₇₄H₁₂₆N₂O₁₁S
• Molecular Weight: 1251.89

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

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

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

There total 6 articles about Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{5-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-2,2-dimethyl-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: 95.0%

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) + 2,2-dimethylcyclohexan-5-on-1-yl 2,3,4,6-tetra-O-lauroyl-1-thio-β-D-galactopyranoside (215312-92-8) → Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{5-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-2,2-dimethyl-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester (215313-32-9)

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran; acetonitrile; for 73h;

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

Reference yield:

n-dodecanoyl chloride (112-16-3) → Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{5-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-2,2-dimethyl-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester (215313-32-9)

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: 75 percent / Et₂NH / CH₂Cl₂ / 3 h

4: 95 percent / 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:

4,4-dimethylcyclohexenone (1073-13-8) → Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{5-[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-2,2-dimethyl-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester (215313-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / Et₂NH / CH₂Cl₂ / 3 h

2: 95 percent / NaCNBH₃ / acetonitrile; tetrahydrofuran / 73 h

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

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

upstream raw materials:

(S)-tryptophan methyl ester hydrochloride

2,2-dimethylcyclohexan-5-on-1-yl 2,3,4,6-tetra-O-lauroyl-1-thio-β-D-galactopyranoside

4,4-dimethylcyclohexenone

n-dodecanoyl chloride

Downstream raw materials:

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

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