3,5-di-O-benzyl-2-O-trifluoromethanesulfonyl-D-xylono-γ-lactone

Base Information

• Chemical Name: 3,5-di-O-benzyl-2-O-trifluoromethanesulfonyl-D-xylono-γ-lactone
• CAS No.: 131139-08-7
• Molecular Formula: C₂₀H₁₉F₃O₇S
• Molecular Weight: 460.428
• Mol file: 131139-08-7.mol

Synonyms:3,5-di-O-benzyl-2-O-trifluoromethanesulfonyl-D-xylono-γ-lactone

Chemical Property of 3,5-di-O-benzyl-2-O-trifluoromethanesulfonyl-D-xylono-γ-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-di-O-benzyl-2-O-trifluoromethanesulfonyl-D-xylono-γ-lactone

There total 6 articles about 3,5-di-O-benzyl-2-O-trifluoromethanesulfonyl-D-xylono-γ-lactone 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: 92.0%

trifluoromethylsulfonic anhydride (358-23-6) + (3R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxydihydrofuran-2(3H)-one (131139-04-3) → 3,5-di-O-benzyl-2-O-trifluoromethanesulfonyl-D-xylono-γ-lactone (131139-08-7)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1016/S0040-4039(00)97734-7

Reference yield:

benzyl bromide (100-39-0) → 3,5-di-O-benzyl-2-O-trifluoromethanesulfonyl-D-xylono-γ-lactone (131139-08-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / NaH / dimethylformamide

2: aqueous CF₃CO₂H

3: Br₂, BaCO₃ / dioxane; H₂O

4: 92 percent / pyridine / CH₂Cl₂

With pyridine; bromine; sodium hydride; barium carbonate; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97734-7

Reference yield:

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (41341-99-5) → 3,5-di-O-benzyl-2-O-trifluoromethanesulfonyl-D-xylono-γ-lactone (131139-08-7)

Guidance literature:

Multi-step reaction with 3 steps

1: aqueous CF₃CO₂H

2: Br₂, BaCO₃ / dioxane; H₂O

3: 92 percent / pyridine / CH₂Cl₂

With pyridine; bromine; barium carbonate; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water;

DOI:10.1016/S0040-4039(00)97734-7

upstream raw materials:

trifluoromethylsulfonic anhydride

(3R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxydihydrofuran-2(3H)-one

3,5-di-O-benzyl-D-xylofuranose

benzyl bromide

Downstream raw materials:

(2R,4R)-3-Benzyloxy-2,4-bis-benzyloxymethyl-oxetane

((2R,3R,4R)-3-Benzyloxy-4-benzyloxymethyl-oxetan-2-yl)-methanol

2,4-anhydro-3,5-di-O-benzyl-D-lyxonic acid

methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate