Benzoic acid (2R,3S,4S,6S)-6-benzyloxy-6-furan-2-yl-4-hydroxy-2-((S)-1-phenylselanyl-ethyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,6S)-6-benzyloxy-6-furan-2-yl-4-hydroxy-2-((S)-1-phenylselanyl-ethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 92622-36-1
• Molecular Formula: C₃₁H₃₀O₆Se
• Molecular Weight: 577.536
• Mol file: 92622-36-1.mol

Synonyms:Benzoic acid (2R,3S,4S,6S)-6-benzyloxy-6-furan-2-yl-4-hydroxy-2-((S)-1-phenylselanyl-ethyl)-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3S,4S,6S)-6-benzyloxy-6-furan-2-yl-4-hydroxy-2-((S)-1-phenylselanyl-ethyl)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4S,6S)-6-benzyloxy-6-furan-2-yl-4-hydroxy-2-((S)-1-phenylselanyl-ethyl)-tetrahydro-pyran-3-yl ester

There total 10 articles about Benzoic acid (2R,3S,4S,6S)-6-benzyloxy-6-furan-2-yl-4-hydroxy-2-((S)-1-phenylselanyl-ethyl)-tetrahydro-pyran-3-yl ester 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:

diphenyl diselenide (1666-13-3) → Benzoic acid (2R,3S,4S,6S)-6-benzyloxy-6-furan-2-yl-4-hydroxy-2-((S)-1-phenylselanyl-ethyl)-tetrahydro-pyran-3-yl ester (92622-36-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) bromine; 2.) HCl (5percent) / 1.) THF, room temp., 10 min; 2.) 0 deg C, 1 h

2: 2.) trifluoroacetic acid (TFA) / 1.) boron trifluoride etherate (BF₃*Et₂O) / 1.) dichloromethane, -78 deg C, 20 min; 2.) 1 h

3: 98 percent / ceric chloride heptahydrate, sodium borohydride / CH₂Cl₂; ethanol / 2 h / -78 - -20 °C

4: 94 percent / 2,6-lutidine, sodium bicarbonate, triethylamine / CH₂Cl₂ / 0.5 h / -78 °C

5: camphorsulfonic acid (CSA) / toluene / 3 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; ceric chloride heptahydrate; camphor-10-sulfonic acid; bromine; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; boron trifluoride diethyl etherate; In ethanol; dichloromethane; toluene;

DOI:10.1021/ja00291a030

Reference yield:

benzoyloxyacetic acid (614-44-8) → Benzoic acid (2R,3S,4S,6S)-6-benzyloxy-6-furan-2-yl-4-hydroxy-2-((S)-1-phenylselanyl-ethyl)-tetrahydro-pyran-3-yl ester (92622-36-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / thionyl chloride / 3 h / Heating

2: 1.) hexamethyldisilazane, N-butyllithium; 2.) HCl (2N) / 1.) THF, 0 deg C, 1 h; 2.) toluene, -78 deg C, 35 min

3: 100 percent / diethyl ether / 0.67 h / 0 °C

4: 100 percent / triethylamine (Et₃N) / diethyl ether / 1.) -78 deg C, 10 min; 2.) room temp., 0.5 h

5: 2.) trifluoroacetic acid (TFA) / 1.) boron trifluoride etherate (BF₃*Et₂O) / 1.) dichloromethane, -78 deg C, 20 min; 2.) 1 h

6: 98 percent / ceric chloride heptahydrate, sodium borohydride / CH₂Cl₂; ethanol / 2 h / -78 - -20 °C

7: 94 percent / 2,6-lutidine, sodium bicarbonate, triethylamine / CH₂Cl₂ / 0.5 h / -78 °C

8: camphorsulfonic acid (CSA) / toluene / 3 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; ceric chloride heptahydrate; camphor-10-sulfonic acid; sodium hydrogencarbonate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; boron trifluoride diethyl etherate; In diethyl ether; ethanol; dichloromethane; toluene;

DOI:10.1021/ja00291a030

Reference yield:

2-benzoyloxyacetyl chloride (54150-57-1) → Benzoic acid (2R,3S,4S,6S)-6-benzyloxy-6-furan-2-yl-4-hydroxy-2-((S)-1-phenylselanyl-ethyl)-tetrahydro-pyran-3-yl ester (92622-36-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) hexamethyldisilazane, N-butyllithium; 2.) HCl (2N) / 1.) THF, 0 deg C, 1 h; 2.) toluene, -78 deg C, 35 min

2: 100 percent / diethyl ether / 0.67 h / 0 °C

3: 100 percent / triethylamine (Et₃N) / diethyl ether / 1.) -78 deg C, 10 min; 2.) room temp., 0.5 h

4: 2.) trifluoroacetic acid (TFA) / 1.) boron trifluoride etherate (BF₃*Et₂O) / 1.) dichloromethane, -78 deg C, 20 min; 2.) 1 h

5: 98 percent / ceric chloride heptahydrate, sodium borohydride / CH₂Cl₂; ethanol / 2 h / -78 - -20 °C

6: 94 percent / 2,6-lutidine, sodium bicarbonate, triethylamine / CH₂Cl₂ / 0.5 h / -78 °C

7: camphorsulfonic acid (CSA) / toluene / 3 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; ceric chloride heptahydrate; camphor-10-sulfonic acid; sodium hydrogencarbonate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; boron trifluoride diethyl etherate; In diethyl ether; ethanol; dichloromethane; toluene;

DOI:10.1021/ja00291a030

upstream raw materials:

(2S*,3S*,4R*)-3-(benzoyloxy)-6-(α-furyl)-2-<(1-phenylseleno)ethyl>-4-<(trimethylsilyl)oxy>-2,3-dihydro-4H-pyran

benzyl alcohol

diphenyl diselenide

benzoyloxyacetic acid

Downstream raw materials:

(2R*,4R*,5S*,6S*)-4,5-bis(acetyloxy)-2-(benzyloxy)-2-(α-furyl)-6-<(phenylseleno)ethyl>tetrahydropyran