methyl (allyl 7,8-O-benzylidene-3-deoxy-β-D-manno-2-octulopyranosid)onate

Base Information

• Chemical Name: methyl (allyl 7,8-O-benzylidene-3-deoxy-β-D-manno-2-octulopyranosid)onate
• CAS No.: 138840-64-9
• Molecular Formula: C₁₉H₂₄O₈
• Molecular Weight: 380.395
• Mol file: 138840-64-9.mol

Synonyms:methyl (allyl 7,8-O-benzylidene-3-deoxy-β-D-manno-2-octulopyranosid)onate

Chemical Property of methyl (allyl 7,8-O-benzylidene-3-deoxy-β-D-manno-2-octulopyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (allyl 7,8-O-benzylidene-3-deoxy-β-D-manno-2-octulopyranosid)onate

There total 7 articles about methyl (allyl 7,8-O-benzylidene-3-deoxy-β-D-manno-2-octulopyranosid)onate 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: 64.0%

benzaldehyde dimethyl acetal (1125-88-8) + methyl (allyl 3-deoxy-β-D-manno-2-octulopyranosid)onate (114850-71-4) → methyl (allyl 7,8-O-benzylidene-3-deoxy-β-D-manno-2-octulopyranosid)onate (138840-64-9)

Guidance literature:

With (+)-10-camphorsulfonic acid; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1246/bcsj.64.3267

Reference yield:

methyl (3aR,4R,7aR)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-carboxylate (114826-98-1) → methyl (allyl 7,8-O-benzylidene-3-deoxy-β-D-manno-2-octulopyranosid)onate (138840-64-9)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

2: 66 percent / 70percent HF-pyridine / CH₂Cl₂ / 1.) -20 deg C, 10 min, 2.) 0 deg C, 10 min

3: 24 percent / N,N-diisopropylethylamine, BF₃ etherate / CH₂Cl₂ / 0.08 h / 0 °C

4: 99 percent / 95percent aq. trifluoroacetic acid (TFA) / CH₂Cl₂ / 1 h / 0 °C

5: 64 percent / (+)-camphorsulfonic acid (CSA) / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; dmap; boron trifluoride diethyl etherate; pyridine hydrogenfluoride; (+)-10-camphorsulfonic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.64.3267

Reference yield:

methyl 3-deoxy-D-manno-2-octulosonate → methyl (allyl 7,8-O-benzylidene-3-deoxy-β-D-manno-2-octulopyranosid)onate (138840-64-9)

Guidance literature:

Multi-step reaction with 6 steps

1: p-toluenesulfonic acid monohydrate / 13 h / Ambient temperature

2: pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

3: 66 percent / 70percent HF-pyridine / CH₂Cl₂ / 1.) -20 deg C, 10 min, 2.) 0 deg C, 10 min

4: 24 percent / N,N-diisopropylethylamine, BF₃ etherate / CH₂Cl₂ / 0.08 h / 0 °C

5: 99 percent / 95percent aq. trifluoroacetic acid (TFA) / CH₂Cl₂ / 1 h / 0 °C

6: 64 percent / (+)-camphorsulfonic acid (CSA) / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; dmap; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; (+)-10-camphorsulfonic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.64.3267

upstream raw materials:

benzaldehyde dimethyl acetal

methyl (allyl 3-deoxy-β-D-manno-2-octulopyranosid)onate

methyl (3aR,4R,7aR)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-carboxylate

methyl (3-deoxy-4,5;7,8-di-O-isopropylidene-α-D-mannooct-2-ulopyranosyl)onate fluoride

Downstream raw materials:

methyl -3-deoxy-β-D-manno-2-octulopyranosid>onate

methyl -3-deoxy-β-D-manno-2-octulopyranosid>onate