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
![3. Formation of trichloroacetimidate donor
2,2,3,3'4',6,6'-Hepta-O-acetyl-B-D-lactose trichloroacetimidate (3)
OAC
ACO
LOAc
Cl3CCN
Aco
LOAC
K₂CO3
AcO
DCM
OACACO-
OAc
NH
Compound
MW (g/mol) eq
n (mmol)
d (g/ml)
Sugar (crude)
636.55
1
4.71
Trichloroacetonitrile
144.39
8.5
1.44
Potassium carbonate
138.21
3
DCM
84.93
1.33
Apparatus: 50 round bottom flask, N₂ atmosphere
Reaction temperature: RT
Reaction time:
TLC: EtOAc/Tol 1:1 + 1% NET,
Reaction molarity: 0.2 M
The crude sugar is dissolved in dry DCM, trichloroacetonitrile and potassium carbonate are added.
Stirring at RT until starting material is consumed. After complete conversion, the solution is filtered,
concentrated in vacuo (water bath not warmer than 30 °C). Crude is used directly for next reaction.
C26H36018
636.5532
OH
AcO
OACACO-
m (g)
LOAC
OAC
C28H36C13NO 18
780.9403
V (ml)
CCI](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F22738e14-f23d-4c46-b80b-87819f26d7c9%2F78a3bb46-dd88-47b4-9a4d-cfda78e60d6c%2Flplvfzp_processed.jpeg&w=3840&q=75)
Transcribed Image Text:3. Formation of trichloroacetimidate donor
2,2,3,3'4',6,6'-Hepta-O-acetyl-B-D-lactose trichloroacetimidate (3)
OAC
ACO
LOAc
Cl3CCN
Aco
LOAC
K₂CO3
AcO
DCM
OACACO-
OAc
NH
Compound
MW (g/mol) eq
n (mmol)
d (g/ml)
Sugar (crude)
636.55
1
4.71
Trichloroacetonitrile
144.39
8.5
1.44
Potassium carbonate
138.21
3
DCM
84.93
1.33
Apparatus: 50 round bottom flask, N₂ atmosphere
Reaction temperature: RT
Reaction time:
TLC: EtOAc/Tol 1:1 + 1% NET,
Reaction molarity: 0.2 M
The crude sugar is dissolved in dry DCM, trichloroacetonitrile and potassium carbonate are added.
Stirring at RT until starting material is consumed. After complete conversion, the solution is filtered,
concentrated in vacuo (water bath not warmer than 30 °C). Crude is used directly for next reaction.
C26H36018
636.5532
OH
AcO
OACACO-
m (g)
LOAC
OAC
C28H36C13NO 18
780.9403
V (ml)
CCI
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