3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl]cholesterol

Base Information

• Chemical Name: 3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl]cholesterol
• CAS No.: 889129-07-1
• Molecular Formula: C₆₈H₉₂O₁₅
• Molecular Weight: 1149.47
• Mol file: 889129-07-1.mol

Synonyms:3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl]cholesterol

Chemical Property of 3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl]cholesterol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl]cholesterol

There total 6 articles about 3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl]cholesterol 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: 76.0%

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7) + 3β-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)cholesterol (121654-14-6) → 3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl]cholesterol (889129-07-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 0.333333h;

DOI:10.1002/ejoc.200500816

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → 3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl]cholesterol (889129-07-1)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethyldioxirane / acetone; CH₂Cl₂ / 1 h / 20 °C

2: 500 mg / zinc chloride / tetrahydrofuran / -70 - 25 °C

3: 76 percent / TMSOTf / CH₂Cl₂ / 0.33 h

With trimethylsilyl trifluoromethanesulfonate; 3,3-dimethyldioxirane; zinc(II) chloride; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1002/ejoc.200500816

Reference yield:

cholesterol (57-88-5) → 3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl]cholesterol (889129-07-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.25 h

2: aq. NaOH / methanol; dioxane

3: 76 percent / TMSOTf / CH₂Cl₂ / 0.33 h

With sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1002/ejoc.200500816

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate

3β-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)cholesterol

3,4,6-tri-O-benzyl-D-glucal

cholesterol

Downstream raw materials:

3β-O-{2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->2)-[2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)]-4,6-O-benzylidene-β-D-glucopyranosyl}cholestanol

3β-O-{(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-[(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->3)]-4,6-O-benzylidene-β-D-glucopyranosyl}cholesterol

3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-4,6-O-benzylidene-β-D-glucopyranosyl]cholestanol

3β-O-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-4,6-O-benzylidene-β-D-glucopyranosyl]cholesterol