3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE

Base Information

• Chemical Name: 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
• CAS No.: 210100-63-3
• Molecular Formula: C16H22 O6
• Molecular Weight: 310.34
• Mol file: 210100-63-3.mol

Synonyms:

Chemical Property of 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE

Chemical Property:

• PSA: 77.38000
• LogP: 0.80140

Purity/Quality:

98%Min ^*data from raw suppliers

3-ORTHO-BENZYL-1,2-ORTHO-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE

There total 5 articles about 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE 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:

3-O-benzyl-1,2-O-isopropylidene-6-O-triisopropylsilyl-α-D-glucopyranoside (612845-04-2) → (3aR,5R,6R,7S,7aR)-7-Benzyloxy-5-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol (210100-63-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h;

Reference yield:

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose (137915-37-8) → (3aR,5R,6R,7S,7aR)-7-Benzyloxy-5-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol (210100-63-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Bu₂SnO

1.2: tetrabutylammonium iodide

2.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.17 h / 0 °C

2.2: 73 percent / ZnCl₂ / CH₂Cl₂; diethyl ether / 18 h / 20 °C

3.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h

With tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; di(n-butyl)tin oxide; In tetrahydrofuran; dichloromethane; acetone;

Reference yield:

D-glucal (13265-84-4) → (3aR,5R,6R,7S,7aR)-7-Benzyloxy-5-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol (210100-63-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: imidazole

2.1: Bu₂SnO

2.2: tetrabutylammonium iodide

3.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.17 h / 0 °C

3.2: 73 percent / ZnCl₂ / CH₂Cl₂; diethyl ether / 18 h / 20 °C

4.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h

With 1H-imidazole; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; di(n-butyl)tin oxide; In tetrahydrofuran; dichloromethane; acetone;

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-6-O-triisopropylsilyl-α-D-glucopyranoside

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

D-glucal

3-O-benzyl-6-O-triisopropylsilyl-D-glucal

Downstream raw materials:

methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate

Refernces