5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose

Base Information

• Chemical Name: 5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose
• CAS No.: 864858-18-4
• Molecular Formula: C₁₆H₁₉F₃O₇S
• Molecular Weight: 412.384
• Mol file: 864858-18-4.mol

Synonyms:5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose

Chemical Property of 5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose

There total 1 articles about 5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose 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:

trifluoromethylsulfonic anhydride (358-23-6) + (1S,2R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol (155345-99-6) → 5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose (864858-18-4)

Guidance literature:

With pyridine; In dichloromethane; at -15 ℃; for 1h;

DOI:10.1021/jo051047b

Reference yield: 92.0%

5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose (864858-18-4) → [(3aS,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzyl ether (864858-21-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 1h; Heating;

DOI:10.1021/jo051047b

Reference yield:

5-O-benzyl-1,2-O-isopropylidene-3-O-triflyl-α-L-xylofuranose (864858-18-4) → (1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hex-4-yl acetate (864858-33-3)

Guidance literature:

Multi-step reaction with 6 steps

1: DBU / acetonitrile / 80 °C

2: 82 percent / ZnEt₂ / toluene / 0 °C

3: HCl / dioxane / 0 °C

4: CrO₃; acetic anhydride; pyridine / CH₂Cl₂ / 0 °C

5: NaBH₄ / ethanol

6: pyridine

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; diethylzinc; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; ethanol; dichloromethane; toluene; acetonitrile; 2: Simmons-Smith reaction;

DOI:10.1081/NCN-200059796

upstream raw materials:

trifluoromethylsulfonic anhydride

(1S,2R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol

Downstream raw materials:

[(3aS,6aS)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzyl ether

(1S,3S,4S,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hexan-4-ol

(1S,3S,4R,5S)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[3.1.0]hexan-4-ol

[(3aS,4aS,5aS,5bS)-2,2-dimethyltetrahydro-4aH-cyclopropa[4,5]furo[2,3-d][1,3]dioxol-4a-yl]methyl benzyl ether