3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose

Base Information

• Chemical Name: 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose
• CAS No.: 1005004-09-0
• Molecular Formula: C₂₈H₃₂O₅
• Molecular Weight: 448.559
• Mol file: 1005004-09-0.mol

Synonyms:3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose

Chemical Property of 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose

There total 9 articles about 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose 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: 91.0%

3,5,6-tri-O-benzyl-4a-carba-β-D-xylohex-4(4a)-enofuranose → 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose (1005004-09-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; triethylamine; In ethyl acetate; at 20 ℃; for 2h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2011.04.032

Reference yield:

(2R,3R,4R,5S,6R)-1,2,4-tri-O-benzyl-1,2,3,4,5,6-hexahydroxyoct-7-ene → 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose (1005004-09-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridinium p-toluenesulfonate / 0.25 h / 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C / Inert atmosphere

2.2: -60 - 20 °C / Inert atmosphere

3.1: n-butyllithium / hexane; toluene / 0 - 20 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: hydrogenchloride / water; acetic acid / 2.5 h / 80 °C

5.1: Hoveyda-Grubbs catalyst second generation / toluene / 1 h / 60 °C / Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethyl acetate / 2 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; In hexane; dichloromethane; water; acetic acid; ethyl acetate; toluene; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.2: Wittig reaction;

DOI:10.1016/j.carres.2011.04.032

Reference yield:

3,5,6-Tri-O-benzyl-D-glucofuranose (35958-64-6) → 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose (1005004-09-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 0 °C / pH 7 / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / 0.25 h / 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C / Inert atmosphere

3.2: -60 - 20 °C / Inert atmosphere

4.1: n-butyllithium / hexane; toluene / 0 - 20 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: hydrogenchloride / water; acetic acid / 2.5 h / 80 °C

6.1: Hoveyda-Grubbs catalyst second generation / toluene / 1 h / 60 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethyl acetate / 2 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; ethyl acetate; toluene; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.2: Wittig reaction;

DOI:10.1016/j.carres.2011.04.032

upstream raw materials:

(2S,4S,5S,6R)-1,2,4-tri-O-benzyl-3-methyleneoct-7-ene-1,2,4,5,6-pentaol

1,2-di-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-xylohex-4(4a)-enofuranose

3,5,6-Tri-O-benzyl-D-glucofuranose

Downstream raw materials:

C₃₂H₃₈O₅S

3,5,6-tri-O-benzyl-1-deoxy-1-S-ethyl-1-thio-4a-carba-β-D-galactofuranose

C₆₃H₇₄O₁₃

C₅₈H₆₄O₁₁