1,6-Anhydro-2,3-di-O-benzyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-β-D-galactopyranose

Base Information

• Chemical Name: 1,6-Anhydro-2,3-di-O-benzyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-β-D-galactopyranose
• CAS No.: 168103-52-4
• Molecular Formula: C₃₇H₄₂O₆Si
• Molecular Weight: 610.822
• Mol file: 168103-52-4.mol

Synonyms:

Chemical Property of 1,6-Anhydro-2,3-di-O-benzyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-β-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-Anhydro-2,3-di-O-benzyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-β-D-galactopyranose

There total 1 articles about 1,6-Anhydro-2,3-di-O-benzyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-β-D-galactopyranose 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:

1,6-Anhydro-2,3-di-O-benzyl-β-D-gluco-hexopyrano-4-ulose (138709-45-2) → 1,6-Anhydro-2,3-di-O-benzyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-β-D-galactopyranose (168103-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) NaHCO₃, aq. H₂O₂ / 1.) THF, -78 deg C, 30 min; -78 deg C to -15 deg C 2 h, 2.) THF, MeOH, reflux, 12 h

2: 100 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; dihydrogen peroxide; sodium hydrogencarbonate; In N,N-dimethyl-formamide;

DOI:10.1021/jo961534e

Reference yield:

1,6-Anhydro-2,3-di-O-benzyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-β-D-galactopyranose (168103-52-4) → (1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol (185155-21-9)

Guidance literature:

Multi-step reaction with 9 steps

1: Ac₂O / 1.5 h / 68 °C

2: MeONa / methanol / 2 h / Ambient temperature

3: 1.) p-TsOH, 2.) Celite, 4A NS, PDC / 2.) CH₂Cl₂, room temperature, 3 h

4: 1.) CeCl₃, 3.) 2N HCl / 1.) THF, Et₂O, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 6 h, 3.) THF, reflux, 3 h

5: 1.) DMSO, TFAA, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) -78 deg C to room temperature, 30 min

6: 1.) t-BuLi / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 1 h

7: 98 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

8: 1.) CeCl₃ / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 3 h

9: TBAF / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; hydrogenchloride; dipyridinium dichromate; cerium(III) chloride; Celite; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium methylate; acetic anhydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo961534e

Reference yield:

1,6-Anhydro-2,3-di-O-benzyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-β-D-galactopyranose (168103-52-4) → (1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarbaldehyde (185155-22-0)

Guidance literature:

Multi-step reaction with 10 steps

1: Ac₂O / 1.5 h / 68 °C

2: MeONa / methanol / 2 h / Ambient temperature

3: 1.) p-TsOH, 2.) Celite, 4A NS, PDC / 2.) CH₂Cl₂, room temperature, 3 h

4: 1.) CeCl₃, 3.) 2N HCl / 1.) THF, Et₂O, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 6 h, 3.) THF, reflux, 3 h

5: 1.) DMSO, TFAA, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) -78 deg C to room temperature, 30 min

6: 1.) t-BuLi / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 1 h

7: 98 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

8: 1.) CeCl₃ / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 3 h

9: TBAF / tetrahydrofuran / 1 h / 0 °C

10: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; hydrogenchloride; dipyridinium dichromate; cerium(III) chloride; Celite; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium methylate; acetic anhydride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo961534e

upstream raw materials:

1,6-Anhydro-2,3-di-O-benzyl-β-D-gluco-hexopyrano-4-ulose

Downstream raw materials:

(1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol

(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarbaldehyde

(1S,3S,4R,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-4-furan-2-yl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarbaldehyde

(1S,3R,4R,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-4-furan-2-yl-3,5-bis-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol