methyl (methyl 5-acetamido-4-O-benzyl-9-O-tert-butyldimethylsilyl-3,5-dideoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)onate

Base Information

Chemical Name:methyl (methyl 5-acetamido-4-O-benzyl-9-O-tert-butyldimethylsilyl-3,5-dideoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)onate
CAS No.:129034-15-7
Molecular Formula:C₂₉H₄₇NO₉Si
Molecular Weight:581.779
Hs Code.:

methyl (methyl 5-acetamido-4-O-benzyl-9-O-tert-butyldimethylsilyl-3,5-dideoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)onate

Synonyms:

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Chemical Property of methyl (methyl 5-acetamido-4-O-benzyl-9-O-tert-butyldimethylsilyl-3,5-dideoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)onate

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Technology Process of methyl (methyl 5-acetamido-4-O-benzyl-9-O-tert-butyldimethylsilyl-3,5-dideoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)onate

There total 23 articles about methyl (methyl 5-acetamido-4-O-benzyl-9-O-tert-butyldimethylsilyl-3,5-dideoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)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:

: 7001-18-5
methyl 2-methoxyacrylate

: 129034-15-7
methyl (methyl 5-acetamido-4-O-benzyl-9-O-tert-butyldimethylsilyl-3,5-dideoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)onate

Guidance literature:: Multi-step reaction with 12 steps

1: 73 percent / toluene / 72 h / 60 °C / 5250420 Torr

2: 82 percent / potassium carbonate / methanol / 3 h

3: 74 percent / silver oxide / CH₂Cl₂ / 1) RT, 30 min; 2) reflux, 11 h

4: 85 percent / Raney nickel / tetrahydrofuran / 0.33 h / Ambient temperature

5: 1) borane-dimethylsulfide; 2) 10 percent aq. sodium hydroxide, 35 percent H₂O₂ / 1) tetrahydrofuran, -10 deg C then RT, 26 h; 2) -10 deg C, then RT, 20 min

6: 83 percent / imidazole / CH₂Cl₂ / ice bath

7: 95 percent / DCC, DMSO, pyridine, trifluoroacetic acid / diethyl ether / 0 deg C, 15 min then RT, 1 h

8: 36 percent / NaBH₄ / methanol / 2 h / -30 °C

9: 78 percent / pyridine / CH₂Cl₂ / 18 h / -20 °C

10: 95 percent / sodium azide / toluene / 40 h

11: Pd/CaCO₃/PbO, H₂ / methanol / 43 h / Ambient temperature

12: pyridine / 24 h

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; Lindlar catalyst; sodium azide; dimethylsulfide borane complex; hydrogen; dihydrogen peroxide; nickel; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

Reference yield:

: 129034-01-1
5-deoxy-2,3-O-isopropylidene-5-phenylthio-D-lyxitol

: 129034-15-7
methyl (methyl 5-acetamido-4-O-benzyl-9-O-tert-butyldimethylsilyl-3,5-dideoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)onate

Guidance literature:: Multi-step reaction with 17 steps

1: 92 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

2: 98 percent / DMSO, dicyclohexyl carbodiimide, pyridine, trifluoroacetic acid / diethyl ether / 0 deg C then RT, 3 h

3: 82 percent / 3 h / 70 °C

4: 96 percent / aq. sodium hydroxide / ethanol / 3.5 h

5: 99 percent / pyridine / toluene / 1) -10 deg C, 30 min; 2) 0 deg C, 17 h

6: 73 percent / toluene / 72 h / 60 °C / 5250420 Torr

7: 82 percent / potassium carbonate / methanol / 3 h

8: 74 percent / silver oxide / CH₂Cl₂ / 1) RT, 30 min; 2) reflux, 11 h

9: 85 percent / Raney nickel / tetrahydrofuran / 0.33 h / Ambient temperature

10: 1) borane-dimethylsulfide; 2) 10 percent aq. sodium hydroxide, 35 percent H₂O₂ / 1) tetrahydrofuran, -10 deg C then RT, 26 h; 2) -10 deg C, then RT, 20 min

11: 83 percent / imidazole / CH₂Cl₂ / ice bath

12: 95 percent / DCC, DMSO, pyridine, trifluoroacetic acid / diethyl ether / 0 deg C, 15 min then RT, 1 h

13: 36 percent / NaBH₄ / methanol / 2 h / -30 °C

14: 78 percent / pyridine / CH₂Cl₂ / 18 h / -20 °C

15: 95 percent / sodium azide / toluene / 40 h

16: Pd/CaCO₃/PbO, H₂ / methanol / 43 h / Ambient temperature

17: pyridine / 24 h

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; Lindlar catalyst; sodium azide; dimethylsulfide borane complex; hydrogen; dihydrogen peroxide; nickel; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

: 129034-00-0
5-deoxy-2,3-O-isopropylidene-5-phenylthio-α-D-lyxofuranose

: 129034-15-7
methyl (methyl 5-acetamido-4-O-benzyl-9-O-tert-butyldimethylsilyl-3,5-dideoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)onate

Guidance literature:: Multi-step reaction with 18 steps

1: 83 percent / NaBH₄ / methanol / 3 h

2: 92 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

3: 98 percent / DMSO, dicyclohexyl carbodiimide, pyridine, trifluoroacetic acid / diethyl ether / 0 deg C then RT, 3 h

4: 82 percent / 3 h / 70 °C

5: 96 percent / aq. sodium hydroxide / ethanol / 3.5 h

6: 99 percent / pyridine / toluene / 1) -10 deg C, 30 min; 2) 0 deg C, 17 h

7: 73 percent / toluene / 72 h / 60 °C / 5250420 Torr

8: 82 percent / potassium carbonate / methanol / 3 h

9: 74 percent / silver oxide / CH₂Cl₂ / 1) RT, 30 min; 2) reflux, 11 h

10: 85 percent / Raney nickel / tetrahydrofuran / 0.33 h / Ambient temperature

11: 1) borane-dimethylsulfide; 2) 10 percent aq. sodium hydroxide, 35 percent H₂O₂ / 1) tetrahydrofuran, -10 deg C then RT, 26 h; 2) -10 deg C, then RT, 20 min

12: 83 percent / imidazole / CH₂Cl₂ / ice bath

13: 95 percent / DCC, DMSO, pyridine, trifluoroacetic acid / diethyl ether / 0 deg C, 15 min then RT, 1 h

14: 36 percent / NaBH₄ / methanol / 2 h / -30 °C

15: 78 percent / pyridine / CH₂Cl₂ / 18 h / -20 °C

16: 95 percent / sodium azide / toluene / 40 h

17: Pd/CaCO₃/PbO, H₂ / methanol / 43 h / Ambient temperature

18: pyridine / 24 h

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; Lindlar catalyst; sodium azide; dimethylsulfide borane complex; hydrogen; dihydrogen peroxide; nickel; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;