methyl-4,6-dideoxy-2,3-O-isopropylidene-4-methylpyranoside

Base Information

• Chemical Name: methyl-4,6-dideoxy-2,3-O-isopropylidene-4-methylpyranoside
• CAS No.: 105678-16-8
• Molecular Formula: C₁₁H₂₀O₄
• Molecular Weight: 216.277
• Mol file: 105678-16-8.mol

Synonyms:4H-1,3-Dioxolo[4,5-c]pyran,a-L-mannopyranoside deriv.

Chemical Property of methyl-4,6-dideoxy-2,3-O-isopropylidene-4-methylpyranoside

Chemical Property:

• Vapor Pressure: 0.0188mmHg at 25°C
• Boiling Point: 261.4°Cat760mmHg
• Flash Point: 90.7°C
• Density: 1.07g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-4,6-dideoxy-2,3-O-isopropylidene-4-methylpyranoside

There total 3 articles about methyl-4,6-dideoxy-2,3-O-isopropylidene-4-methylpyranoside 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: 80.0%

(3aR,4R,6S,7aR)-4-Methoxy-2,2,6-trimethyl-7-methylene-tetrahydro-[1,3]dioxolo[4,5-c]pyran → (3aR,4R,6S,7R,7aR)-4-Methoxy-2,2,6,7-tetramethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (105678-16-8)

Guidance literature:

With Schwartz's reagent; In benzene; for 0.0833333h; Heating;

DOI:10.1007/BF00952937

Reference yield:

1,6-anhydro-3-O-benzyl-2-deoxy-2,4-di-C-methyl-β-D-allopyranose (97321-54-5) → (3aR,4R,6S,7R,7aR)-4-Methoxy-2,2,6,7-tetramethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (105678-16-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH, imidazole / 1.) THF, 30 min, 2.) 10 deg C, 30 min, 3.) 1 h

2: Bu₃SnH, AIBN / toluene / 0.5 h / Heating

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In toluene;

DOI:10.1007/BF00952937

Reference yield:

1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-4-O-methylthiothiocarbonyl-β-allopyranose (105678-10-2) → (3aR,4R,6S,7R,7aR)-4-Methoxy-2,2,6,7-tetramethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (105678-16-8) + (3aR,4R,6S,7S,7aR)-4-Methoxy-2,2,6,7-tetramethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1007/BF00952937

upstream raw materials:

1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-4-O-methylthiothiocarbonyl-β-allopyranose

1,6-anhydro-3-O-benzyl-2-deoxy-2,4-di-C-methyl-β-D-allopyranose

Refernces