(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane Chemical Properties

Boiling point:

427.9±40.0 °C(Predicted)

Density 

1.17

storage temp. 

Sealed in dry,2-8°C

solubility 

Benzene, Chloroform, DMSO, Methanol

form 

Oil

color 

Colorless to Pale Yellow

InChI

InChI=1S/C20H22O3/c1-3-7-15(8-4-1)12-21-14-17-18(11-19-20(17)23-19)22-13-16-9-5-2-6-10-16/h1-10,17-20H,11-14H2/t17-,18+,19-,20+/m1/s1

InChIKey

YPDRJNPIGFCETD-WCIQWLHISA-N

SMILES

[C@]12([H])[C@]([H])(O1)C[C@H](OCC1=CC=CC=C1)[C@H]2COCC1=CC=CC=C1

CAS DataBase Reference

110567-22-1(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HS Code 

29329990

(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane Usage And Synthesis

Chemical Properties

Colorless Oil

Uses

Entecavir intermediate.

Synthesis

General procedure: sodium hydride (55-65%, 0.93 kg, 21.3-25.2 mol) was suspended in anhydrous tetrahydrofuran (25 kg) and stirred for 10 min at room temperature. A solution of (1S,2R,3S,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-ol (2.99 kg, 12.3 mol) in tetrahydrofuran was added slowly and dropwise at 20-30 °C. Subsequently, benzyl bromide (3.14 kg, 18.3 mol) was added dropwise over 2-3 hours at room temperature. After completion of the reaction, the reaction was quenched by the addition of anhydrous ethanol (1.5 kg) and stirred at 10 °C. The solvent was removed by distillation under reduced pressure and the residue was dissolved in ethyl acetate. The resulting solution was washed with saturated saline (10 kg, 3 times) and the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give (1S,2R,3S,5R)-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane (4.4 kg) as a reddish brown oil.1H NMR (400 MHz, DMSO-d6). δ 1.923-1.960 (1H, m), 2.026-2.087 (1H, m), 2.448-2.436 (1H, m), 3.324-3.520 (3H, m), 3.520 (1H, s), 3.865-3.884 (1H, m), 4.322-4.391 (2H, m), 4.480 (2H, s), 7.251-7.373 (10H, m). HRMS (ESI): m/z calcd for C20H22O3Na [M+Na]+ 333.1467, found 333.1463.

References

[1] Synthesis, 2003, # 13, p. 2101 - 2109
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 549 - 554
[3] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2009, vol. 52, # 11, p. 485 - 489
[5] Organic Preparations and Procedures International, 2017, vol. 49, # 6, p. 568 - 574

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