methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate

Base Information

Chemical Name:methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate
CAS No.:1590365-52-8
Molecular Formula:C₂₅H₃₅NO₁₃
Molecular Weight:557.552
Hs Code.:

Synonyms:methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate

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Chemical Property of methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate

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Technology Process of methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate

There total 10 articles about methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate 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:

: 1151942-33-4
C₂₆H₃₁NO₁₂S

: 108-93-0
cyclohexanol

: 1590365-50-6
methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

: 1590365-52-8
methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate

Guidance literature:: C₂₆H₃₁NO₁₂S; With di(p-tolyl) sulfoxide; In dichloromethane; at -70 ℃; for 0.25h; Molecular sieve; Inert atmosphere;

With trifluoromethylsulfonic anhydride; In dichloromethane; at -70 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

cyclohexanol; In dichloromethane; at -70 - -50 ℃; for 4h; Overall yield = 61 %; stereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.carres.2014.02.006

Reference yield:

: 1246533-58-3
C₂₆H₃₁NO₁₂S

: 108-93-0
cyclohexanol

: 1590365-50-6
methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

: 1590365-52-8
methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate

Guidance literature:: C₂₆H₃₁NO₁₂S; With di(p-tolyl) sulfoxide; In dichloromethane; at -70 ℃; for 0.25h; Molecular sieve; Inert atmosphere;

With trifluoromethylsulfonic anhydride; In dichloromethane; at -70 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

cyclohexanol; In dichloromethane; at -70 - -50 ℃; for 4h; Overall yield = 67 %; stereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.carres.2014.02.006

Reference yield:

: 108740-39-2,6931-68-6,72690-21-2,73208-82-9,108740-37-0,108740-38-1,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,74006-95-4
(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

: 1590365-50-6
methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

: 1590365-52-8
methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate

Guidance literature:: Multi-step reaction with 6 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 0 °C / Inert atmosphere

2.1: methanesulfonic acid / methanol / Reflux

3.1: sodium hydrogencarbonate / acetonitrile; water / 0 °C

4.1: acetic anhydride; pyridine / 0 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

6.1: di(p-tolyl) sulfoxide / dichloromethane / 0.25 h / -70 °C / Molecular sieve; Inert atmosphere

6.2: 0.5 h / -70 °C / Molecular sieve; Inert atmosphere

6.3: 4 h / -70 - -50 °C / Molecular sieve; Inert atmosphere

With pyridine; methanesulfonic acid; di(p-tolyl) sulfoxide; boron trifluoride diethyl etherate; acetic anhydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1016/j.carres.2014.02.006