Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-D-threo-L-galacto-heptit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside

Base Information

• Chemical Name: Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-D-threo-L-galacto-heptit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside
• CAS No.: 174175-65-6
• Molecular Formula: C₅₈H₇₅NO₁₁Si
• Molecular Weight: 990.319

Synonyms:

Chemical Property of Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-D-threo-L-galacto-heptit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-D-threo-L-galacto-heptit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside

There total 22 articles about Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-D-threo-L-galacto-heptit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside 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:

thexyldimethylsilyl 2-azido-2-deoxy-β-D-glucopyranoside (157488-88-5) → Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-D-threo-L-galacto-heptit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside (174175-65-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / p-TsOH / acetonitrile / 1 h

2: 93 percent / NaH / dimethylformamide / 2 h / -15 °C

3: 86 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran

4: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

5: acetonitrile / 1 h / 35 °C

6: 36 percent / 1 M DIBALH / toluene; CH₂Cl₂ / 1.) -70 deg C, 2 h, 2.) -70 deg C to r.t., 4 h

7: 64 percent / Et₃N / 18 h / 60 °C

8: 56 percent / LDA / tetrahydrofuran; hexane / 1.) THF, hexane, -100 deg C, 30 min, 2.) HMPA, THF, 1 h

9: Raney nickel W II / tetrahydrofuran / 7 h

10: pyridine / Ambient temperature

11: 1 M NaOMe / methanol / 2 h / Ambient temperature

12: 1.) H₃B*SMe₂, 2.) 10percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 3 d, 2.) 1 h

With pyridine; hydrogenchloride; sodium hydroxide; dimethylsulfide borane complex; Raney nickel W II; dihydrogen peroxide; sodium methylate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-D-threo-L-galacto-heptit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside (174175-65-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / p-TsOH / acetonitrile / 1 h

2: 93 percent / NaH / dimethylformamide / 2 h / -15 °C

3: 86 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran

4: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

5: acetonitrile / 1 h / 35 °C

6: 36 percent / 1 M DIBALH / toluene; CH₂Cl₂ / 1.) -70 deg C, 2 h, 2.) -70 deg C to r.t., 4 h

7: 64 percent / Et₃N / 18 h / 60 °C

8: 56 percent / LDA / tetrahydrofuran; hexane / 1.) THF, hexane, -100 deg C, 30 min, 2.) HMPA, THF, 1 h

9: Raney nickel W II / tetrahydrofuran / 7 h

10: pyridine / Ambient temperature

11: 1 M NaOMe / methanol / 2 h / Ambient temperature

12: 1.) H₃B*SMe₂, 2.) 10percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 3 d, 2.) 1 h

With pyridine; hydrogenchloride; sodium hydroxide; dimethylsulfide borane complex; Raney nickel W II; dihydrogen peroxide; sodium methylate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

Thexyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside → Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-D-threo-L-galacto-heptit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside (174175-65-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 93 percent / NaH / dimethylformamide / 2 h / -15 °C

2: 86 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran

3: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

4: acetonitrile / 1 h / 35 °C

5: 36 percent / 1 M DIBALH / toluene; CH₂Cl₂ / 1.) -70 deg C, 2 h, 2.) -70 deg C to r.t., 4 h

6: 64 percent / Et₃N / 18 h / 60 °C

7: 56 percent / LDA / tetrahydrofuran; hexane / 1.) THF, hexane, -100 deg C, 30 min, 2.) HMPA, THF, 1 h

8: Raney nickel W II / tetrahydrofuran / 7 h

9: pyridine / Ambient temperature

10: 1 M NaOMe / methanol / 2 h / Ambient temperature

11: 1.) H₃B*SMe₂, 2.) 10percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 3 d, 2.) 1 h

With pyridine; hydrogenchloride; sodium hydroxide; dimethylsulfide borane complex; Raney nickel W II; dihydrogen peroxide; sodium methylate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

benzaldehyde dimethyl acetal

benzyl bromide

thexyldimethylsilyl 2-azido-2-deoxy-β-D-glucopyranoside

Thexyldimethylsilyl 2-azido-3,6-di-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranoside

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