methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-arabinonate

Base Information

• Chemical Name: methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-arabinonate
• CAS No.: 787572-17-2
• Molecular Formula: C₁₄H₁₅F₃O₇S
• Molecular Weight: 384.33
• Mol file: 787572-17-2.mol

Synonyms:methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-arabinonate

Chemical Property of methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-arabinonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-arabinonate

There total 9 articles about methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-arabinonate 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: 98.0%

trifluoromethylsulfonic anhydride (358-23-6) + methyl 2,4-anhydro-5-O-benzyl-D-arabinonate (357400-96-5) → methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-arabinonate (787572-17-2)

Guidance literature:

With pyridine; In dichloromethane; at -30 - -10 ℃; for 1h;

DOI:10.1016/j.tetasy.2004.07.031

Reference yield:

D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-arabinonate (787572-17-2)

Guidance literature:

Multi-step reaction with 8 steps

1: potassium carbonate; bromine / H₂O

2: 19.0 g / hydrochloric acid / 20 °C

3: 96 percent / pyridine / CH₂Cl₂ / 2.25 h / -30 - -10 °C

4: 75 percent / potassium carbonate / 4 h / -25 - -20 °C

5: 83 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0 - 20 °C

6: 97 percent / pyridine / CH₂Cl₂ / 0.75 h / -30 - -10 °C

7: 99 percent / caesium trifluoroacetate / butan-2-one / 16 h / 60 °C

8: 98 percent / pyridine / CH₂Cl₂ / 1 h / -30 - -10 °C

With pyridine; hydrogenchloride; triethylsilane; bromine; cesium trifluoroacetate; potassium carbonate; trifluoroacetic acid; In dichloromethane; water; butanone;

DOI:10.1016/j.tetasy.2004.07.031

Reference yield:

(S)-3,5-O-benzylidene-2-O-trifluoromethanesulfonyl-D-xylono-1,4-lactone (130481-72-0) → methyl 2,4-anhydro-5-O-benzyl-3-O-trifluoromethanesulfonyl-D-arabinonate (787572-17-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / potassium carbonate / 4 h / -25 - -20 °C

2: 83 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0 - 20 °C

3: 97 percent / pyridine / CH₂Cl₂ / 0.75 h / -30 - -10 °C

4: 99 percent / caesium trifluoroacetate / butan-2-one / 16 h / 60 °C

5: 98 percent / pyridine / CH₂Cl₂ / 1 h / -30 - -10 °C

With pyridine; triethylsilane; cesium trifluoroacetate; potassium carbonate; trifluoroacetic acid; In dichloromethane; butanone;

DOI:10.1016/j.tetasy.2004.07.031

upstream raw materials:

trifluoromethylsulfonic anhydride

methyl 2,4-anhydro-5-O-benzyl-D-arabinonate

D-Xylose

(S)-3,5-O-benzylidene-2-O-trifluoromethanesulfonyl-D-xylono-1,4-lactone