1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-3-O-benzyl-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-3-O-benzyl-β-D-glucopyranose
• CAS No.: 81076-89-3
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 81076-89-3.mol

Synonyms:1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-3-O-benzyl-β-D-glucopyranose

Chemical Property of 1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-3-O-benzyl-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-3-O-benzyl-β-D-glucopyranose

There total 10 articles about 1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-3-O-benzyl-β-D-glucopyranose 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: 94.0%

(1S,2S,3S,4R,5R)-2,4-Dimethyl-6,8-dioxabicyclo<3.2.1>octan-3-ol (76690-23-8) + benzyl bromide (100-39-0) → 1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-3-O-benzyl-β-D-glucopyranose (81076-89-3)

Guidance literature:

With sodium hydride; tetra-(n-butyl)ammonium iodide;

DOI:10.1016/S0040-4039(00)85401-5

Reference yield:

1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-β-D-galactopyranose (81076-77-9) → 1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-3-O-benzyl-β-D-glucopyranose (81076-89-3)

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-mesyl-β-D-galactopyranose (81076-80-4) → 1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-3-O-benzyl-β-D-glucopyranose (81076-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / i-PrNEt₂ / nitromethane / 32 h / Heating

2: 1.) Cp₂Zr(H)Cl, 1N HCl / 1.) benzene, 2.) 20 deg C

With hydrogenchloride; Schwartz's reagent; N,N-diethyl-N-isopropylamine; In nitromethane;

DOI:10.1007/BF00958406

upstream raw materials:

(1S,2S,3S,4R,5R)-2,4-Dimethyl-6,8-dioxabicyclo<3.2.1>octan-3-ol

benzyl bromide

1,6-anhydro-3-O-benzyl-2,4-dideoxy-2-C-methyl-4-methylene-β-D-xylohexopyranose

(1S,2S,3S,4S,5R)-2-Methyl-3,4-epoxy-6,8-dioxabicyclo<3.2.1>octan-3-ol

Downstream raw materials:

(2S,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-methyl-hexane-1,2-diol

(2R,3S,4R)-3-Benzyloxy-4-[1,3]dithian-2-yl-2-methyl-pentan-1-ol

methyl-α-3-O-benzyl-2,4,6-tridesoxy-2,4-di-C-methyl-D-glucopyranoside

methyl-α-3-O-benzyl-2,4-didesoxy-2,4-di-C-methyl-D-glucopyranoside