[ CAS No. 85960-55-0 ]

Name: 85960-55-0|(2S)-2-[2-(Benzyloxy)ethyl]oxirane|95%
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Quality Control of [ 85960-55-0 ]

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Product Details of [ 85960-55-0 ]

CAS No. :	85960-55-0	MDL No. :	MFCD27930213
Formula :	C₁₁H₁₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WEEINLJFNLBGTR-NSHDSACASA-N
M.W :	178.23	Pubchem ID :	6917466
Synonyms :

Safety of [ 85960-55-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P202-P201-P264-P280-P302+P352-P308+P313-P337+P313-P305+P351+P338-P362+P364-P332+P313-P405	UN#:	N/A
Hazard Statements:	H315-H319-H341	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 85960-55-0 ]

* 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 [ 85960-55-0 ]

[ 85960-55-0 ] Synthesis Path-Downstream 1~69

1
[ 112-92-5 ]
[ 85960-55-0 ]
[ 149035-19-8 ]

Reference： [1]Canadian Journal of Chemistry,1993,vol. 71,p. 206 - 209

2
(S)-4-benzyloxy-1,2-butanediol [ No CAS ]
[ 85960-55-0 ]

Yield	Reaction Conditions	Operation in experiment
		The following Example illustrates synthesis of (S)-2-[2-(benzyloxy)ethyl]oxirane which is useful for the preparation of 5-dodecene-1,3-diol via the chemical synthesis route disclosed herein below in Example 5. This is a prophetic Example. (S)-2-[2-(benzyloxy)ethyl]oxirane will be prepared via a literature procedure (see e.g., Cink, R. D.; Forsyth, C. J. J. Org. Chem 1995, 60, 8122). Briefly, to a magnetically stirred solution of S-4-(benzyloxy)butane-1,2-diol (207 mg, 1.05 mmol, CAS No.69985-32-6) in THF (10.6 mL) at 0 C. will be added NaH (63 mg, 2.6 mmol). The resulting mixture will be warmed to room temperature and stirred for 1 hour, then cooled to 0 C. before N-tosylimidazole (237 mg, 1.07 mmol) is added in three equal portions over 20 min. The mixture will be allowed to warm to room temperature and stirred for 45 min before being recooled to 0 C. Sat. aq. NH4Cl and Et2O (65 mL) will then be added, the separated organic phase will be washed with H2O (25 mL) and brine (25 mL), and the combined aqueous layers will be extracted with Et2O (2*25 mL). The combined organic layers will then be dried (Na2SO4), filtered, and concentrated by rotary evaporation. Chromatography (silica gel; hexanes/EtOAc 5:1) of the residue is expected to provide the desired product.

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 2101 - 2104
[2]Synthetic Communications,1993,vol. 23,p. 285 - 289
[3]Tetrahedron Asymmetry,1996,vol. 7,p. 3255 - 3262
[4]Tetrahedron Asymmetry,2007,vol. 18,p. 975 - 981
[5]Organic Letters,2006,vol. 8,p. 3655 - 3657
[6]Journal of Chemical Research, Miniprint,1983,p. 217 - 228
[7]Journal of the Chemical Society. Chemical communications,1985,p. 1386 - 1388
[8]Canadian Journal of Chemistry,1993,vol. 71,p. 206 - 209
[9]Patent: US2018/72645,2018,A1 .Location in patent: Paragraph 0203-0204
[10]Patent: EP3342768,2018,A1

3
[ 1826-67-1 ]
[ 85960-55-0 ]
(R)-1-benzyloxy-hex-5-en-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper(l) iodide; In tetrahydrofuran; at -20℃; for 4h;Inert atmosphere;	Copper iodide (0.53 g, 2.79 mmol, 0.1 eq)was gentlyheated under vacuum and slowly cooled under nitrogenatmosphere, then 10 cm3 THF was added and the resultingsuspension was cooled to -20 C and 55 cm3 vinylmagnesium bromide (29.04 mmol, 1.1 eq) was added atthe same temperature while stirring. A solution of 4.8 gepoxide 5 (27.90 mmol, 1.0 eq) in 20 cm3 dry THF wasadded to the above reagent and the mixture was stirred at-20 C for 1 h. After completion of the reaction, thereaction was quenched with saturated aqueous NH4Cl,extracted into EtOAc (3 9 30 cm3), the combined organiclayer was washed with brine, dried over Na2SO4, andconcentrated, to give the crude product which was purifiedby column chromatography (silica gel, 60-120 mesh, 15 %EtOAc in pet. ether) to afford 11 (5.1 g, 88 %) as acolorless liquid [a]D25 = ?3.3 (c = 1, CHCl3).

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 2101 - 2104
[2]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4657 - 4663
[3]Monatshefte fur Chemie,2015,vol. 146,p. 1921 - 1926
[4]Angewandte Chemie - International Edition,2000,vol. 39,p. 4279 - 4281
[5]Organic Letters,2012,vol. 14,p. 3408 - 3411

4
[ 13291-18-4 ]
[ 85960-55-0 ]
[ 101906-15-4 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1985,p. 1386 - 1388
[2]Organic Letters,2006,vol. 8,p. 3655 - 3657

5
[ 85960-54-9 ]
[ 85960-55-0 ]

Reference： [1]Canadian Journal of Chemistry,1993,vol. 71,p. 206 - 209
[2]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4657 - 4663
[3]Journal of the Chemical Society. Chemical communications,1985,p. 1386 - 1388
[4]Organic Letters,2006,vol. 8,p. 3655 - 3657

6
[ 85960-55-0 ]
[ 75-26-3 ]
[ 101906-15-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2171 - 2182

7
[ 125975-36-2 ]
[ 85960-55-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In methanol; at 20℃; for 1.25h;	A mixture of (S)-4-benzyloxy-2-hydroxybutyl methanesulfonate (the reference compound 1-1, 12.3 g, 44.8 mmol), potassium carbonate (12.3 g, 89.0 mmol) and methanol (100 mL) was stirred at room temperature for 75 minutes. After removing the solvent under reduced pressure, 0.5N sodium hydroxide (450 mL) and ethyl acetate (200 mL) were added to the residue. The mixture was distributed, and the aqueous layer was extracted with ethyl acetate (100 mL×2). The organic layers were combined, and washed with a saturated saline solution (100 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the titled reference compound (8.0 g) (quantitative). [tabl0002-en] [Table 2] Reference compound 2-1 1H-NMR (400MHz, CDCl3) δ 7.41-7.27 (5H, m), 4.53 (2H, s), 3.69-3.58 (2H, m), 3.12-3.04 (1H, m), 2.79 (1H, dd, J = 5. 1, 4.0 Hz), 2.53 (1H, dd, J = 5.1, 2.7 Hz), 1.98-1.86 (1H, m), 1.84-1.72 (1H, m)

Reference： [1]Patent: EP3342768,2018,A1 .Location in patent: Paragraph 0111
[2]Synthetic Communications,1995,vol. 25,p. 331 - 342
[3]Tetrahedron Asymmetry,2007,vol. 18,p. 975 - 981

8
[ 3068-00-6 ]
[ 636-61-3 ]
benzylating reagent [ No CAS ]
[ 115114-87-9 ]
[ 85960-55-0 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 2262 - 2264

9
[ 3068-00-6 ]
[ 97-67-6 ]
benzylating reagent [ No CAS ]
[ 115114-87-9 ]
[ 85960-55-0 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 2262 - 2264

10
[ 1216963-74-4 ]
[ 85960-55-0 ]
[ 214483-90-6 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 6770 - 6771

11
[ 6089-04-9 ]
[ 85960-55-0 ]
[ 362623-87-8 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 4907 - 4911

12
[ 94426-72-9 ]
[ 85960-55-0 ]
(R)-4-phenylmethoxy-1,2-butanediol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%; 49%	With (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); In water; at 0 - 20℃; for 18h;	To an ice-cooled solution of compound 3 (5.0 g, 0.028 mol) in dry CH2Cl2 (50 ml)mCPBA (14.9 g, 0.056 mol) was added in portions over a period of 30 min at 0 C. Aftercomplete addition of mCPBA, cooling was removed and stirring was continued at roomtemperature for 24 h. The reaction mixture was diluted with dichloromethane (50 ml)and washed with an aqueous sodium bicarbonate, followed by water. Organic layer wasdried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crudeproduct which was purified by column chromatography (silica gel; pet. ether/EtOAc90/10) to yield racemic epoxide 4 (4.91 g, 89%) as colorless liquid. IR (Neat):3384, 2926, 2879, 1718, 1492, 1452, 1276, 1113, 1026, 756 cm1; 1H NMR (200 MHz,CDCl3): d 1.742.02 (m, 2H), 2.51 (dd, J2.2 and 4.8 Hz, 1H), 2.78 (t, J4.8 Hz,1H), 3.053.14 (m, 1H), 3.62 (t, J6.8 Hz, 2H), 4.53 (s, 2H), 7.297.37 (m, 5H); 13CNMR (CDCl3): d 138.2, 128.3, 127.5, 126.8, 73.0, 66.5, 50.0, 47.0, 32.9; HRMS (ESI) m/zcalcd for C11H14O2Na [(MNa)] 201.0886, found 201.0887. A mixture of racemicepoxide (5.0 g, 0.028 mol) and (S,S) salen Co(III)OAc complex-A (0.10 g, 0.015 mmol)were vigorously stirred for 15 min at 0 C and water (0.3 ml, 0.017 mol) was added overa period of 1 h, through syringe. The reaction mixture was stirred at r.t. and monitoredby HPLC (Kromasil 5-cellucoat column) UV: 220 nm, 3% isopropanol in n-hexane. Thereaction mixture was diluted with EtOAc, dried over anhydrous Na2SO4 and evaporatedunder reduced pressure. The residue was purified by column chromatography (silicagel; pet. ether/EtOAc93/7). The less polar (S)-epoxide 5 eluted first as colorless liquid(2.12 g, 42%); [a]D12.2 (c3, CHCl3) {lit.9f [a]D-15.6 (c1.25, CHCl3)}; ee >99%[chiral HPLC analysis; Kromasil 5-cellucoat column (2504.6 cm) column; eluent: hexane/isopropanol97/3; flow rate: 1.0 ml/min; detector: 220nm (tR13.47 min),(tS14.08 min)]; 1H NMR (200 MHz, CDCl3): d 1.742.02 (m, 2H), 2.52 (dd, J2.2and 4.8 Hz, 1H), 2.80 (t, J4.8 Hz, 1H), 3.053.14 (m, 1H), 3.64 (t, J6.8 Hz, 2H),4.55 (s, 2H), 7.297.37 (m, 5H); 13C NMR (CDCl3): d 138.2, 128.3, 127.5, 126.8, 73.0,66.5, 50.0, 47.0, 32.9; HRMS (ESI) m/z calcd for C11H14O2Na [(MNa)] 201.0886,found 201.0887. Followed by the (R)-diol 6 as a colorless liquid(2.71 g,49%);[a]D5.5 (c1, CHCl3), ee >99% [chiral HPLC analysis; Kromasil RP-18(1504.6 cm) column; eluent: H2O/MeOH40/60; flow rate: 1.0 ml/min; detector:254nm (tR2.98 min)]; IR (Neat): 3386, 2925, 2867, 1453, 1096, 759, 698 cm1; 1HNMR (200 MHz, CDCl3): d 1.661.85 (m, 2H), 3.46 (dd, J6.9 and 11.4 Hz, 1H),3.563.71 (m, 3H), 3.833.94 (m, 1H), 4.52 (s, 2H), 7.247.40 (m, 5H); 13C NMR(50 MHz, CDCl3): d 137.7, 128.4, 127.7, 127.6, 73.2, 70.2, 68.1, 65.5, 34.1; HRMS (ESI)m/z calcd for C11H14O2Na [(MNa)] 201.0886, found 201.0887.
44%; 39%	With Jacobsen's catalyst; In tetrahydrofuran; water; at 0 - 25℃; for 22h;	A mixture of 0.21 g (S,S)-(-)-N,N1-bis(3,5-ditert-butylsalicyclidene)-1,2-cyclohexanediaminocobalt(II)(0.31 mmol, 0.005 eq), toluene, and 0.04 cm3 AcOH(0.63 mmol, 0.01 eq) was stirred while open to the air for1 h at 25 C. The solvent was removed under reducedpressure and the brown residue was dried over highvacuum. The oxirane 9a (11 g, 63.95 mmol, 1.0 eq) wasadded in one portion, the stirred mixture was cooled in anice water bath. Water (0.63 cm3, 35.17 mmol, 0.55 eq)was slowly added and the temperature of the reactionmixture was maintained in such a way that it never risesmore than 20 C. After completion of reaction within onehour, removed the ice bath. Now the reaction mixture wasstirred for 22 h at room temperature and finally the residuewas purified by column chromatography to afford theepoxide 10 (4.9 g, 44 %) as colorless oil [a]D25 = -18.8(c = 0.8, CHCl3).

Reference： [1]Synthetic Communications,2018,vol. 48,p. 2093 - 2098
[2]Tetrahedron Letters,2009,vol. 50,p. 1328 - 1330
[3]Monatshefte fur Chemie,2015,vol. 146,p. 1921 - 1926
[4]Tetrahedron Letters,2001,vol. 42,p. 4907 - 4911
[5]Tetrahedron Letters,2008,vol. 49,p. 6765 - 6767
[6]Chirality,2013,vol. 25,p. 965 - 969
[7]Journal of the American Chemical Society,2002,vol. 124,p. 1307 - 1315

13
[ 94426-72-9 ]
(S)-4-benzyloxy-1,2-butanediol [ No CAS ]
[ 115114-87-9 ]
[ 85960-55-0 ]
(R)-4-phenylmethoxy-1,2-butanediol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 7010 - 7014

14
[ 94426-72-9 ]
(S)-4-benzyloxy-1,2-butanediol [ No CAS ]
[ 85960-55-0 ]
(R)-4-phenylmethoxy-1,2-butanediol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 1307 - 1315
[2]Journal of the American Chemical Society,2002,vol. 124,p. 1307 - 1315

15
[ 85960-55-0 ]
[ 116137-78-1 ]
[ 521309-77-3 ]

Reference： [1]Chemical Communications,2003,p. 228 - 229

16
[ 55695-90-4 ]
[ 85960-55-0 ]
[ 521309-77-3 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 11939 - 11951

17
[ 85960-55-0 ]
[ 82511-02-2 ]
[ 862814-66-2 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 3255 - 3258

18
[ 3536-96-7 ]
[ 85960-55-0 ]
(R)-1-benzyloxy-hex-5-en-3-ol [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 3681 - 3688
[2]Organic Letters,2005,vol. 7,p. 4819 - 4822

19
[ 2622-05-1 ]
[ 85960-55-0 ]
[ 869348-19-6 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 4819 - 4822

20
[ 94426-72-9 ]
[ 115114-87-9 ]
[ 85960-55-0 ]
(R)-4-phenylmethoxy-1,2-butanediol [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 4819 - 4822

21
[ 2181-42-2 ]
[ 85960-55-0 ]
[ 117661-29-7 ]

Reference： [1]Synlett,2014,vol. 25,p. 501 - 504
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 5510 - 5515
[3]Synthesis,2011,p. 3343 - 3349

22
[ 88180-26-1 ]
[ 85960-55-0 ]
4-benzyloxy-1-(2-pent-4-enyl-[1,3]dithian-2-yl)-butan-2-ol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 2602 - 2611

23
[ 85960-55-0 ]
[ 77564-44-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;	To a cooled suspension of LAH (0.770 g,0.02mol) in 20 mL dry THF was added a solution of compound 15 (3 g, 0.0168mol) in 5 mL THF slowly drop by drop. After completeaddition of starting material it was stirred for another 20 minutes at 0oCand quenched with saturated solution of sodium sulphate, filtered through a padof celite, washed with ethyl acetate, then concentrated by evaporation ofsolvent followed by dry flash columnchromatography to afford a alcohol 16(2.9g, 96%) as colorless oil; IR(KBr): 3407, 3030, 2966, 2864, 1454, 1368, 1098, 1027, 891, 864, 745, 702 cm-1; [a]D32 +38 (c 1, CHCl3); H1 NMR (300 MHz, CDCl3): δ= 7.23-7.34 (m, 5H), 4.47-4.49 (m, 2H),3.92-4.01 (m, 1H), 3.63-3.69 (m, 1H), 3.55-3.62 (m, 1H), 3.17 (bs, 1H), 1.62-1.78(m, 2H), 1.17 (q, J= 1.37 Hz, 3H); 13CNMR (75 MHz, CDCl3): δ=137.7,128.2, 127.4, 127.3, 72.9, 68.5, 66.7, 37.9, 23.0; MS (ESI): m/z = 181 [M+H]+, 203 [M+Na].

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 5629 - 5631
[2]Synlett,2007,p. 1945 - 1947

24
[ 5470-84-8 ]
[ 85960-55-0 ]

Reference： [1]Synlett,2014,vol. 25,p. 501 - 504
[2]Tetrahedron Asymmetry,2007,vol. 18,p. 975 - 981

25
[ 85960-55-0 ]
[ 91285-64-2 ]

Reference： [1]Tetrahedron Asymmetry,2007,vol. 18,p. 975 - 981
[2]Angewandte Chemie - International Edition,1998,vol. 37,p. 187 - 190

26
[ 70388-33-9 ]
[ 85960-55-0 ]

Reference： [1]Synthesis,2006,p. 1863 - 1867
[2]Tetrahedron Letters,2014,vol. 55,p. 5629 - 5631
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 9821 - 9837
[4]Patent: US2020/283364,2020,A1

27
[ 94426-72-9 ]
[ 85960-55-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With (R,R)-(-)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II); acetic acid; In tetrahydrofuran; water; at 0 - 20℃; for 16h;	To a solution of (±)-compound 32 (3.1 g, 17.0 mmol) in THF (1 mL) were added (S,S)-(+)-N,AP-bis (3,5-di-tert-butylsalicyclidene)-1,2-cyclohexanediaminocobalt(II) (0.21 g, 0.4 mmol) and AcOH (80 μL, 1.4 mmol). The reaction mixture was cooled to 0 C., and H2O (0.17 mL, 9.5 mmol) was added in one portion. The reaction mixture was allowed to warm to room temperature and stirred for 16 h. The reaction mixture was quenched with H2O and extracted with EtOAc. The combined organic layer was washed with water (50 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (hexane/EtOAc=12:1 to 3:1) to furnish compound 33 (1.5 g, 50%) as a pale yellow oil. Rf=0.51 (hexane/EtOAc=7:1, v/v). 1H NMR (300 MHz, CDCl3) δ7.43-7.23 (m, 5H), 4.56 (s, 2H), 3.65 (q, J=5.6 Hz, 2H), 3.10 (brs, 1H), 2.78 (brs, 1H), 2.55 (brs, 1H), 1.97-1.76 (m, 2H).
4.8 g	With (R,R)-(-)-N,N′-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminocobalt(II); acetic acid; In tetrahydrofuran; water; at 0 - 20℃; for 24h;Inert atmosphere; Resolution of racemate;	The racemic epoxide of 16 (10 g, 56 mmol) and THF (0.5 mL) were added to (R,R)-Salen-CoIII catalyst (0.17 g, 0.28 mmol) and the solution was cooled to 0 C. Then acetic acid (0.1 mL, 1.12 mmol) was added and after 5 min, water (0.5 mL, 30.8 mmol) was added. After another 5 min, the ice bath was removed and the reaction mixture was stirred at rt for 24 h. The reaction mixture was then concentrated in vacuo. The compound was purified by column chromatography to afford epoxide (S)-16 (4.8 g) as a pale yellow liquid. Rf = 0.8 (silicagel, 60-120 mesh, 60% Hexane/EtOAc); 1H NMR (CDCl3, 300 MHz): δ 1.67-1.78 (m, 1H), 1.82-1.93 (m, 1H), 2.45-2.47 (m, 1H), 2.71-2.74 (m, 1H), 2.98-3.04 (m, 1H), 3.55-3.60 (m, 2H), 4.49 (s, 1H), 7.21-7.28 (m, 5H); 13C NMR (CDCl3, 75 MHz): δ 32.99, 47.13, 50.09, 67.05, 73.10, 127.65, 128.44, 138.30; IR (neat): υ 2922, 2854, 772 cm-1; (c 0.7, CHCl3); ESI-MS: m/z: 179 [M+H].

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9821 - 9837
[2]Patent: US2020/283364,2020,A1 .Location in patent: Paragraph 0032; 0121-0122
[3]Tetrahedron Letters,2012,vol. 53,p. 115 - 118
[4]Organic Letters,2010,vol. 12,p. 3394 - 3397
[5]Synthesis,2006,p. 1863 - 1867
[6]Tetrahedron Asymmetry,2012,vol. 23,p. 1155 - 1160,6

28
[ 85960-55-0 ]
[ 910488-36-7 ]