Dodecanoic acid (2S,3R,4S,5S,6R)-2-[2-(tert-butoxycarbonylmethyl-amino)-cyclohexylsulfanyl]-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Dodecanoic acid (2S,3R,4S,5S,6R)-2-[2-(tert-butoxycarbonylmethyl-amino)-cyclohexylsulfanyl]-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 215313-09-0
• Molecular Formula: C₆₆H₁₂₁NO₁₁S
• Molecular Weight: 1136.75

Synonyms:Dodecanoic acid (2S,3R,4S,5S,6R)-2-[2-(tert-butoxycarbonylmethyl-amino)-cyclohexylsulfanyl]-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Dodecanoic acid (2S,3R,4S,5S,6R)-2-[2-(tert-butoxycarbonylmethyl-amino)-cyclohexylsulfanyl]-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Dodecanoic acid (2S,3R,4S,5S,6R)-2-[2-(tert-butoxycarbonylmethyl-amino)-cyclohexylsulfanyl]-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-tetrahydro-pyran-3-yl ester

There total 4 articles about Dodecanoic acid (2S,3R,4S,5S,6R)-2-[2-(tert-butoxycarbonylmethyl-amino)-cyclohexylsulfanyl]-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-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: 93.0%

glycine tert-butyl ester hydrochloride (27532-96-3) + cyclohexan-2-on-1-yl 2,3,4,6-tetra-O-lauroyl-1-thio-β-D-galactopyranoside (215312-94-0) → Dodecanoic acid (2S,3R,4S,5S,6R)-2-[2-(tert-butoxycarbonylmethyl-amino)-cyclohexylsulfanyl]-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-tetrahydro-pyran-3-yl ester (215313-09-0)

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)-2-[2-(tert-butoxycarbonylmethyl-amino)-cyclohexylsulfanyl]-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-tetrahydro-pyran-3-yl ester (215313-09-0)

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: 93 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:

D-Galactose (10257-28-0) → Dodecanoic acid (2S,3R,4S,5S,6R)-2-[2-(tert-butoxycarbonylmethyl-amino)-cyclohexylsulfanyl]-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-tetrahydro-pyran-3-yl ester (215313-09-0)

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: 93 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

upstream raw materials:

glycine tert-butyl ester hydrochloride

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

n-dodecanoyl chloride

D-Galactose

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