methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

Base Information

Chemical Name:methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate
CAS No.:1449035-95-3
Molecular Formula:C₃₃H₄₈N₄O₁₁
Molecular Weight:676.764
Hs Code.:

methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

Synonyms:methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

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Chemical Property of methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

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Technology Process of methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

There total 11 articles about methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate 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: 72.0%

: 1449035-94-2
methyl 5-acetamido-2,6-anhydro-4-amino-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

: 152120-54-2,862686-58-6,1143572-00-2
N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine

: 1449035-95-3
methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

Guidance literature:: With triethylamine; In tetrahydrofuran; methanesulfonic acid; at 20 ℃; for 168h; Inert atmosphere;
DOI:10.1016/j.bmc.2013.05.054

Reference yield:

: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-α/β-D-erythro-L-gluco-non-2-ulopyranosonate

: 1449035-95-3
methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

Guidance literature:: Multi-step reaction with 8 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 48 h / 40 °C / Inert atmosphere

2: dmap; pyridine / 16 h / 20 °C / Inert atmosphere

3: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 2 h / 60 °C / Inert atmosphere

4: trifluoroacetic acid; water / ethyl acetate / 16 h / 20 °C

5: diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 7.25 h / 5 - 20 °C / Inert atmosphere

6: sodium methylate / methanol / 1 h / 20 °C / Inert atmosphere

7: hydrogen sulfide / pyridine / 16 h / 20 °C

8: triethylamine / tetrahydrofuran; methanesulfonic acid / 168 h / 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; trimethylsilyl trifluoromethanesulfonate; diphenylphosphoranyl azide; hydrogen sulfide; water; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; methanesulfonic acid; dichloromethane; ethyl acetate; benzene;
DOI:10.1016/j.bmc.2013.05.054

Reference yield:

: 622-97-9,24936-41-2
1-ethenyl-4-methylbenzene

: 1449035-95-3
methyl 5-acetamido-2,6-anhydro-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-3-C-[3'-(p-tolyl)prop-2'-enyl]-D-glycero-D-galacto-non-2-enonate

Guidance literature:: Multi-step reaction with 8 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 48 h / 40 °C / Inert atmosphere

2: dmap; pyridine / 16 h / 20 °C / Inert atmosphere

3: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 2 h / 60 °C / Inert atmosphere

4: trifluoroacetic acid; water / ethyl acetate / 16 h / 20 °C

5: diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 7.25 h / 5 - 20 °C / Inert atmosphere

6: sodium methylate / methanol / 1 h / 20 °C / Inert atmosphere

7: hydrogen sulfide / pyridine / 16 h / 20 °C

8: triethylamine / tetrahydrofuran; methanesulfonic acid / 168 h / 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; trimethylsilyl trifluoromethanesulfonate; diphenylphosphoranyl azide; hydrogen sulfide; water; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; methanesulfonic acid; dichloromethane; ethyl acetate; benzene;
DOI:10.1016/j.bmc.2013.05.054