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ChemicalBook > Product Catalog >Pharmaceutical intermediates >Bulk Drug Intermediates >(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane

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

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Products Intro: Product Name:(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane
CAS:110567-22-1
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Products Intro: Product Name:(1S,2R,3S,5R)-3-(Benzyloxy)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexane
CAS:110567-22-1
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Products Intro: Product Name:(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane
CAS:110567-22-1
Purity:0.99 Package:1kg 5kg 10kg 218kg kilograms per barrel

(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane manufacturers
(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane Basic information
Product Name:(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane
Synonyms:(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane;(1S,2R,3S,5R)-3-(Phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane;[1S-(1a,2a,3,5a)]-3-(Phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane;6-Oxabicyclo[3.1.0]hexane, 3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-, (1S, 2R, 3S, 5R);(1S,2R,3S,5R)-3-(Benzyloxymethyl)-6-oxabicyclo[3.1.0]hexane;(1S,2R,3S,5R)-3-(Phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane ,90%;1R,2R-2-[(Phenylmethoxy)methyl]-3-cyclo penten-1-ol;[1S-(1α,2α,3β,5α)]-3-(Phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane
CAS:110567-22-1
MF:C20H22O3
MW:310.39
EINECS:1592732-453-0
Product Categories:Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:110567-22-1.mol
(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane Structure
(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
InChIInChI=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
InChIKeyYPDRJNPIGFCETD-WCIQWLHISA-N
SMILES[C@]12([H])[C@]([H])(O1)C[C@H](OCC1=CC=CC=C1)[C@H]2COCC1=CC=CC=C1
CAS DataBase Reference110567-22-1(CAS DataBase Reference)
Safety Information
Safety Statements 24/25
HS Code 29329990
MSDS Information
(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane Usage And Synthesis
Chemical PropertiesColorless Oil
UsesEntecavir intermediate.
Synthesis
Benzyl bromide

100-39-0

(1S,2R,3S,5R)-2-(Benzyloxymethyl)-6-oxabicyclo[3.1.0]hexan-3-ol

117641-39-1

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

110567-22-1

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
Tag:(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane(110567-22-1) Related Product Information
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