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Chemical Structure| 31139-36-3 Chemical Structure| 31139-36-3

Structure of Dibenzyl dicarbonate
CAS No.: 31139-36-3

Chemical Structure| 31139-36-3

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Product Details of [ 31139-36-3 ]

CAS No. :31139-36-3
Formula : C16H14O5
M.W : 286.28
SMILES Code : O=C(OCC1=CC=CC=C1)OC(OCC2=CC=CC=C2)=O
MDL No. :MFCD00043124
InChI Key :FHRRJZZGSJXPRQ-UHFFFAOYSA-N
Pubchem ID :3649378

Safety of [ 31139-36-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 31139-36-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 31139-36-3 ]

[ 31139-36-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 4726-96-9 ]
  • [ 31139-36-3 ]
  • [ 20806-43-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium carbonate; In 1,4-dioxane; water; To a stirred solution of O-benzyl-L-serine (25.0 g, 128 mmole) in water (200 ml) and dioxane (100 ml) was added sodium carbonate (7.46 g, 70 mmole) at room temperature. A solution of dibenzyldicarbonate (36.1 g, 126 mmole) in dioxane (100 ml) was added dropwise and the mixture stirred for 18 hours. Dioxane was evaporated under vacuum and the aqueous residue extracted with diethyl ether. Evaporation of the dried (Na2 SO4) extracts under vacuum gave a white solid which was washed with hexane to yield crude N-benzyloxycarbonyl-O-benzyl-L-serine (39.57 g, 95%).
95% With sodium carbonate; In 1,4-dioxane; water; To a stirred solution of O-benzyl-L-serine (25.0 g, 128 mmole) in water (200 ml) and dioxane (100 ml) was added sodium carbonate (7.46 g, 70 mmole) at room temperature. A solution of dibenzyldicarbonate (36.1 g, 126 mmole) in dioxane (100 ml) was added dropwise and the mixture stirred for 18 hours. Dioxane was evaporated under vacuum and the aqueous residue extracted with diethyl ether. Evaporation of the dried (Na2SO4) extracts under vacuum gave a white solid which was washed with hexane to yield crude N-benzyloxycarbonyl-O-benzyl-L-serine (39.57 g, 95%).
  • 3
  • [ 31139-36-3 ]
  • [ 23356-96-9 ]
  • [ 6216-63-3 ]
  • 4
  • [ 40499-83-0 ]
  • [ 31139-36-3 ]
  • [ 95656-88-5 ]
YieldReaction ConditionsOperation in experiment
47% With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 3h; To the solution of pyrrolidin-3-ol (1.0 g, 11 mmol) in THF (5 mL) and 1M NaOH (5 mL) was added dibenzyldicarbonate (3.3, 11 mmol) at room temperature. The reaction mixture was stirred for 3 h then the THF removed under reduced pressure. The residue was dissolved in DCM (50 mL) and washed successively with saturated NaHCO3 (2×20mL) and saturated NaCl (2×20 mL). The solution was dried over Na2SO4, decanted and concentrated. Benzyl 3-hydroxypyrrolidine-1-carboxylate (1.1 g, 47%) was isolated by prep. HPLC YMC ODSA 30×100 mm, 20-100% MeOH/H2O (0. 1% TFA) gradient over 10 mins at 20 mL/min flow rate at a retention time of 4.93 min. LCMS: 1.21 min [M+1] 222.06 (2 min gradient, MeOH/H2O 0.1% TFA).
 

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