1-<5-<2-(phenylsulfonyl)ethyl>-2α,3β,4β,5α-tetrahydro-3,4-di-O-benzoyl-2H-pyran-2-yl>-2-propanone

Base Information

• Chemical Name: 1-<5-<2-(phenylsulfonyl)ethyl>-2α,3β,4β,5α-tetrahydro-3,4-di-O-benzoyl-2H-pyran-2-yl>-2-propanone
• CAS No.: 112348-43-3
• Molecular Formula: C₃₀H₃₀O₈S
• Molecular Weight: 550.629
• Mol file: 112348-43-3.mol

Synonyms:1-<5-<2-(phenylsulfonyl)ethyl>-2α,3β,4β,5α-tetrahydro-3,4-di-O-benzoyl-2H-pyran-2-yl>-2-propanone

Chemical Property of 1-<5-<2-(phenylsulfonyl)ethyl>-2α,3β,4β,5α-tetrahydro-3,4-di-O-benzoyl-2H-pyran-2-yl>-2-propanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<5-<2-(phenylsulfonyl)ethyl>-2α,3β,4β,5α-tetrahydro-3,4-di-O-benzoyl-2H-pyran-2-yl>-2-propanone

There total 7 articles about 1-<5-<2-(phenylsulfonyl)ethyl>-2α,3β,4β,5α-tetrahydro-3,4-di-O-benzoyl-2H-pyran-2-yl>-2-propanone 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:

benzoyl chloride (98-88-4) → 1-<5-<2-(phenylsulfonyl)ethyl>-2α,3β,4β,5α-tetrahydro-3,4-di-O-benzoyl-2H-pyran-2-yl>-2-propanone (112348-43-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / p-TsOH / toluene / Heating

2: 52 percent / toluene / Heating

3: 76 percent / Et₃N / CH₂Cl₂ / Ambient temperature

4: Rh₂(OAc)4 / CH₂Cl₂ / Ambient temperature

With toluene-4-sulfonic acid; triethylamine; dirhodium tetraacetate; In dichloromethane; toluene;

DOI:10.1021/jo00119a023

Reference yield:

benzyl 2-O-benzoyl-α-D-xylopyranoside (18403-20-8) → 1-<5-<2-(phenylsulfonyl)ethyl>-2α,3β,4β,5α-tetrahydro-3,4-di-O-benzoyl-2H-pyran-2-yl>-2-propanone (112348-43-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / triphenylphosphine, CHI₃, imidazole / toluene / 21 h / Heating

2: 80 percent / NBS, water / dimethylsulfoxide; H₂O / 30 h / Ambient temperature

3: 91 percent / pyridine / 15 h / Ambient temperature

4: 80 percent / tributyltin chloride, cyanoborohydride, AIBN / 2-methyl-propan-2-ol / 4 h / Heating

5: 75 percent / cyclohexene / 10percent Pd/C / methanol / 16 h / Heating

6: 2.) DBU / 1.) acetonitrile, reflux, 48 h, 2.) acetonitrile, 0 deg C, 1 h

With 1H-imidazole; N-Bromosuccinimide; iodoform; 2,2'-azobis(isobutyronitrile); cyanoborane; tributyltin chloride; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; cyclohexene; palladium on activated charcoal; In pyridine; methanol; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;

DOI:10.1021/jo00242a017

Reference yield:

benzyl 4-bromo-4-deoxy-2,3-di-O-benzoyl-β-L-lyxopyranoside (112348-35-3) → 1-<5-<2-(phenylsulfonyl)ethyl>-2α,3β,4β,5α-tetrahydro-3,4-di-O-benzoyl-2H-pyran-2-yl>-2-propanone (112348-43-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / tributyltin chloride, cyanoborohydride, AIBN / 2-methyl-propan-2-ol / 4 h / Heating

2: 75 percent / cyclohexene / 10percent Pd/C / methanol / 16 h / Heating

3: 2.) DBU / 1.) acetonitrile, reflux, 48 h, 2.) acetonitrile, 0 deg C, 1 h

With 2,2'-azobis(isobutyronitrile); cyanoborane; tributyltin chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; cyclohexene; palladium on activated charcoal; In methanol; tert-butyl alcohol;

DOI:10.1021/jo00242a017

upstream raw materials:

C₂₇H₂₆O₈S

1-triphenylphosphoranylidene-2-propanone

benzyl 4-<2-(phenylsulfonyl)ethyl>-4-deoxy-2,3-di-O-benzoyl-β-L-lyxopyranoside

benzyl 2-O-benzoyl-α-D-xylopyranoside