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OAC ACO مامات AcO- OACACO- OAC C28H36Cl3NO 18 780.9403 CCla HO NH BF3 Et20 DCM ACO OAC ACO OACACO- .OAC OAC C28H39CIO 18 699.0515

OAC ACO مامات AcO- OACACO- OAC C28H36Cl3NO 18 780.9403 CCla HO NH BF3 Et20 DCM ACO OAC ACO OACACO- .OAC OAC C28H39CIO 18 699.0515

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter25: Biomolecules: Carbohydrates
Section25.SE: Something Extra
Problem 69AP
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Draw the curly arrow mechanism for this experiment, include all details like electrons, curly arrows, by products etc
4. Glycosylation with chloroethanol acceptor 2-Chloroethyl ACO مایا 2,2,3,3'4',6,6'-Hepta-O-acetyl-B-D-lactopyranoside (4) HO CI ACO OAC AcO- OAC OAC OACACO OAC CC13 ACO NH Compound MW (g/mol) eq n (mmol) d (g/ml) 780.94 1 4.71 Sugar 2-chloroethanol 80.51 4.7 1.20 BF3 Et₂O 141.93 1 1.15 1.33 DCM 84.93 Apparatus: 50 ml round bottom flask, N₂ atmosphere Reaction temperature: RT Reaction time: TLC: EtOAc/Tol 2:1 Reaction molarity: 0.2 M Sugar and 2-chloroethanol are dissolved in dry DCM and put on ice. BF3 Et₂O is added dropwise to the reaction mixture, then allow flask to attain RT. When TLC shows complete conversion of the starting material, the solution is diluted with DCM (25 ml) and poured onto ice water (50 ml). The org. layer is separated (lower fraction!) and washed with water, sat. aq. NaHCO3 and sat. aq. NaCl. The org. layer is dried over MgSO4, filtered and concentrated in vacuo. Purification via chromatography using EtOAc/Tol 2:1. C28H36Cl3NO 18 780.9403 BF3 E1₂0 DCM OACACO- OAC m (g) OAC C28H39 CIO 18 699.0515 v (ml)
Transcribed Image Text:4. Glycosylation with chloroethanol acceptor 2-Chloroethyl ACO مایا 2,2,3,3'4',6,6'-Hepta-O-acetyl-B-D-lactopyranoside (4) HO CI ACO OAC AcO- OAC OAC OACACO OAC CC13 ACO NH Compound MW (g/mol) eq n (mmol) d (g/ml) 780.94 1 4.71 Sugar 2-chloroethanol 80.51 4.7 1.20 BF3 Et₂O 141.93 1 1.15 1.33 DCM 84.93 Apparatus: 50 ml round bottom flask, N₂ atmosphere Reaction temperature: RT Reaction time: TLC: EtOAc/Tol 2:1 Reaction molarity: 0.2 M Sugar and 2-chloroethanol are dissolved in dry DCM and put on ice. BF3 Et₂O is added dropwise to the reaction mixture, then allow flask to attain RT. When TLC shows complete conversion of the starting material, the solution is diluted with DCM (25 ml) and poured onto ice water (50 ml). The org. layer is separated (lower fraction!) and washed with water, sat. aq. NaHCO3 and sat. aq. NaCl. The org. layer is dried over MgSO4, filtered and concentrated in vacuo. Purification via chromatography using EtOAc/Tol 2:1. C28H36Cl3NO 18 780.9403 BF3 E1₂0 DCM OACACO- OAC m (g) OAC C28H39 CIO 18 699.0515 v (ml)
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