methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-gluco-2-nonulopyranosid-5-ulos)onate

Base Information

Chemical Name:methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-gluco-2-nonulopyranosid-5-ulos)onate
CAS No.:129063-70-3
Molecular Formula:C₂₇H₄₂O₉Si
Molecular Weight:538.711
Hs Code.:

Synonyms:methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-gluco-2-nonulopyranosid-5-ulos)onate

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Chemical Property of methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-gluco-2-nonulopyranosid-5-ulos)onate

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Technology Process of methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-gluco-2-nonulopyranosid-5-ulos)onate

There total 18 articles about methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-gluco-2-nonulopyranosid-5-ulos)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: 95.0%

: 129034-10-2
methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)onate

: 129063-70-3
methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-gluco-2-nonulopyranosid-5-ulos)onate

Guidance literature:: With pyridine; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In diethyl ether; 0 deg C, 15 min then RT, 1 h;

Reference yield:

: 7001-18-5
methyl 2-methoxyacrylate

: 129063-70-3
methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-gluco-2-nonulopyranosid-5-ulos)onate

Guidance literature:: Multi-step reaction with 7 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

With pyridine; 1H-imidazole; sodium hydroxide; dimethylsulfide borane complex; 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

: 129063-70-3
methyl (methyl 4-O-benzyl-9-O-tert-butyldimethylsilyl-3-deoxy-7,8-O-isopropylidene-D-gluco-2-nonulopyranosid-5-ulos)onate

Guidance literature:: Multi-step reaction with 12 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

With pyridine; 1H-imidazole; sodium hydroxide; dimethylsulfide borane complex; 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;