Benzyl 3,4-O-isopropylidene-α-D-galactopyranoside

Base Information

• Chemical Name: Benzyl 3,4-O-isopropylidene-α-D-galactopyranoside
• CAS No.: 182622-28-2
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347
• Mol file: 182622-28-2.mol

Synonyms:Benzyl 3,4-O-isopropylidene-α-D-galactopyranoside

Chemical Property of Benzyl 3,4-O-isopropylidene-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 3,4-O-isopropylidene-α-D-galactopyranoside

There total 1 articles about Benzyl 3,4-O-isopropylidene-α-D-galactopyranoside 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: 85.0%

benzyl α-D-galactopyranoside (86196-36-3) + 2,2-dimethoxy-propane (77-76-9) → Benzyl 3,4-O-isopropylidene-α-D-galactopyranoside (182622-28-2)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 5h;

DOI:10.1039/b101234g

Reference yield: 90.0%

benzoyl chloride (98-88-4) + Benzyl 3,4-O-isopropylidene-α-D-galactopyranoside (182622-28-2) → Benzyl 2,6-Di-O-benzoyl-3,4-O-isopropylidene-α-D-galactopyranoside (346420-62-0)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 2h;

DOI:10.1039/b101234g

Reference yield:

Benzyl 3,4-O-isopropylidene-α-D-galactopyranoside (182622-28-2) → Toluene-4-sulfonic acid (2S,5R,6S)-5-methoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (182622-54-4)

Guidance literature:

Multi-step reaction with 15 steps

1: pyridine / 20 h / Ambient temperature

2: 80 percent / aq. AcOH / 4 h / 50 °C

3: 90 percent / acetonitrile / 5 h / Ambient temperature

4: 80 percent / trimethyl phosphite / 4.5 h / Heating

5: 85 percent / H₂ / Pd(OH)2/C / ethanol / 5 h / Ambient temperature

6: 100 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

7: 79 percent / imidazole / dimethylformamide / 0.08 h / Ambient temperature

8: 87 percent / NaOH / acetone / 2 h / Heating

9: 74 percent / BCl₃*SMe₂ / CH₂Cl₂ / 14 h / Ambient temperature

10: 105 mg / CCl₄, Ph₃P / tetrahydrofuran / 3 h / Heating

11: 16 percent / diethyl ether / 1 h / 0 °C

12: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, room temp., 12 h

13: 48 percent / (diacetoxyiodo)benzene, I₂ / cyclohexane / 1.17 h / 40 °C / Irradiation

14: 88 percent / Bu₄NF / tetrahydrofuran / 2.5 h / Ambient temperature

15: 100 percent / pyridine / 15 h / Ambient temperature

With 1H-imidazole; tetrachloromethane; sodium hydroxide; sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; boron trichloride - methyl sulfide complex; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium carbonate; ozone; acetic acid; triphenylphosphine; phosphorous acid trimethyl ester; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo972023a

upstream raw materials:

benzyl α-D-galactopyranoside

2,2-dimethoxy-propane

Downstream raw materials:

benzyl 2,6-di-O-acetyl-3,4-O-isopropylidene-α-D-galactopyranoside

Benzyl 2,6-Di-O-benzoyl-3,4-O-isopropylidene-α-D-galactopyranoside

Benzyl 2,6-Di-O-benzoyl-α-D-galactopyranoside

Benzyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-bezoyl-α-D-galactopyranoside