[ CAS No. 707-07-3 ] {[proInfo.proName]}

Name: 707-07-3|(Trimethoxymethyl)benzene|95%
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Quality Control of [ 707-07-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 707-07-3 ]

Product Details of [ 707-07-3 ]

CAS No. :	707-07-3	MDL No. :	MFCD00008474
Formula :	C₁₀H₁₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IECKAVQTURBPON-UHFFFAOYSA-N
M.W :	182.22	Pubchem ID :	69720
Synonyms :		Chemical Name :	(Trimethoxymethyl)benzene

Calculated chemistry of [ 707-07-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.97
TPSA :	27.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.57
Log Po/w (XLOGP3) :	2.27
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	1.76
Log Po/w (SILICOS-IT) :	1.59
Consensus Log Po/w :	1.96

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.48
Solubility :	0.607 mg/ml ; 0.00333 mol/l
Class :	Soluble
Log S (Ali) :	-2.49
Solubility :	0.592 mg/ml ; 0.00325 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.83
Solubility :	0.271 mg/ml ; 0.00149 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.38

Safety of [ 707-07-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 707-07-3 ]

* 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.

Upstream synthesis route of [ 707-07-3 ]
Downstream synthetic route of [ 707-07-3 ]

[ 707-07-3 ] Synthesis Path-Upstream 1~4

1
[ 64-17-5 ]
[ 707-07-3 ]
[ 1663-61-2 ]

Reference： [1] Chemical Science, 2015, vol. 6, # 2, p. 1399 - 1403
[2] Chemical Science, 2018, vol. 9, # 21, p. 4785 - 4793

2
[ 22158-41-4 ]
[ 707-07-3 ]
[ 63388-44-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	at 90℃; for 2 h;	2-phenylnaphtho[2,3-d]oxazole-4,9-dione (A) Intermediate 3 (500 mg, 1.0 eq), trimethylorthobenzoate (3.6 mL, 8.0 eq) and PPTS (66 mg, 0.1 eq) were combined and heated at 90° C. (oil bath) for 2 hours at which point LC-MS analysis indicated complete consumption of starting material. The reaction mixture was diluted with Et₂O and the resulting yellow ppt collected and washed with Et₂O and EtOAc and dried to yield desired product (472 mg, 65percent) as a bright yellow fluffy solid. ¹H NMR (400 MHz, CDCl₃): δ 7.53-7.62 (3H, M), 7.81 (2H, dd, J=3.5, 5.9), 8.25 (1H, dd, J=3.3, 5.7), 8.29 (1H, dd, J=3.1, 5.9), 8.31-8.34 (2H, M). LRMS (M+H)⁺: 276.19.

Reference： [1] Heterocyclic Communications, 2002, vol. 8, # 2, p. 199 - 204
[2] Patent: US9725425, 2017, B1, . Location in patent: Page/Page column 104; 105

3
[ 420-04-2 ]
[ 707-07-3 ]
[ 6041-23-2 ]

Yield	Reaction Conditions	Operation in experiment
65.30 g	at 135℃; for 0.75 h;	Stage 1: Methyl N-cyanobenzenecarboximidoate (0462) (0463) (Trimethoxymethyl)benzene (75 g) and cyanamide (17.304 g) were taken up in 78 ml of acetic anhydride and then stirred at 135° C. for 45 minutes. The mixture was then concentrated under reduced pressure, the residue was stirred with cyclohexane, and the solids were filtered off with suction and dried. This left 65.30 g of the title compound. HPLC-MS: log P (neutral)=1.83; mass (m/z): 161.1 (M+H)⁺; ¹H NMR (DMSO-D₆) 4.045 (s, 3H), 7.601-7.644 (m, 2H), 7.712-7.755 (m, 1H), 7.966-7.995 (m, 2H).

Reference： [1] Journal of Organic Chemistry, 1963, vol. 28, p. 1816 - 1821
[2] Patent: US2017/73318, 2017, A1, . Location in patent: Paragraph 0462; 0463

4
[ 707-07-3 ]
[ 1168150-46-6 ]

Reference： [1] Patent: CN104003925, 2016, B,

[ 707-07-3 ] Synthesis Path-Downstream 1~88

1
[ 50409-12-6 ]
[ 707-07-3 ]
[ 74091-54-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1545 - 1548
[2]Journal of Organic Chemistry,2019,vol. 84,p. 4112 - 4119
[3]Canadian Journal of Chemistry,1984,vol. 62,p. 1068 - 1073
[4]Chemische Berichte,1953,vol. 86,p. 790,793
[5]Canadian Journal of Chemistry,1980,vol. 58,p. 567 - 573

2
[ 707-07-3 ]
[ 102651-96-7 ]

Reference： [1]Synthetic Communications,1989,vol. 19,p. 2307 - 2312
[2]Monatshefte fur Chemie,1986,vol. 117,p. 375 - 384
[3]Justus Liebigs Annalen der Chemie,1960,vol. 632,p. 38 - 55

3
[ 2302-25-2 ]
[ 707-07-3 ]
[ 127531-13-9 ]

Reference： [1]Canadian Journal of Chemistry,1990,vol. 68,p. 375 - 382

4
[ 3068-00-6 ]
[ 707-07-3 ]
[ 131076-15-8 ]

Reference： [1]Heterocycles,1993,vol. 35,p. 665 - 669

5
[ 42890-76-6 ]
[ 707-07-3 ]
1-Phenyl-2,7,8-trioxa-bicyclo[3.2.1]octane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 4144 - 4150

6
[ 42890-76-6 ]
[ 707-07-3 ]
(1R,5S)-1-Phenyl-2,7,8-trioxa-bicyclo[3.2.1]octane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 4144 - 4150

7
[ 87421-19-0 ]
[ 707-07-3 ]
[ 148906-20-1 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 6969 - 6972
[2]Angewandte Chemie - International Edition,1999,vol. 38,p. 1093 - 1095

8
[ 3068-00-6 ]
[ 707-07-3 ]
(1S,5R)-1-Phenyl-2,7,8-trioxa-bicyclo[3.2.1]octane [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1985,vol. 63,p. 816 - 822

9
(2R,3S)-3-hydroxyleucine methyl ester hydrochloride [ No CAS ]
[ 707-07-3 ]
[ 148906-20-1 ]

Yield	Reaction Conditions	Operation in experiment
77%	In 1,2-dimethoxyethane; at 100℃; for 14h;Heating / reflux;	In a 2-neck round bottom flask (500 mL), fitted with a CaCl2 guard tube, anhydrous MeOH (150 mL) was added and dry HCl was bubbled slowly at 0 C. About 50-60 g of dry HCl was collected. (2R,3S)-3-Hydroxyleucine (27, 7R=isopropyl, 5.0 g, 34 mmol) was added to the methanolic HCl solution in small portions. The reaction mixture was refluxed at 65 C. for 24 h. The reaction flask was cooled to RT and methanol was removed under vacuum to yield a viscous liquid. The viscous liquid was dried under high vacuum for 6 h to furnish the hydrochloride of compound 28 (7R=isopropyl, R=methyl) (6.60 g, 98% yield) as a hygroscopic semi-solid material. To a solution of 28 (6.60 g, 0.033 mol) in DME (100 mL) was added trimethylorthobenzoate (18.25 g, 0.10 mol, 3 eq) and the reaction mixture was refluxed at 100 C. for 8 h. The reaction progress was monitored by TLC and it showed presence of some baseline material. The reaction mixture was refluxed for additional 6 h and then cooled to RT. DME was removed under vaccum and water (100 mL) was added to the viscous residue. Aqueous layer was extracted with ether (2×100 mL). Ether layer was dried (anhyd. Na2SO4) and concentrated under vacuum to furnish a viscous oil. Flash column chromatography on SiO2 afforded the pure oxazoline 21 (6.32 g, 77% yield) as a colorless viscous oil: Rf 0.50 (EtOAc/hexane, 3:7, two runs); H1 NMR 6 CDCl3: 1.0-1.10 (two d, 6H, two CH3), 2.0 (m,1H, -CH-), 3.80 (s, 3H, -COOMe), 4.60 (d, 1H, -CH-), 4.70 (dd, 1H, -CH-), 7.40-7.60 (m, 3H, aromatic H), 8.0 (d, 2H, aromatic H)

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 3584 - 3590
[2]Patent: US2005/203162,2005,A1 .Location in patent: Page/Page column 22

10
[ 182803-48-1 ]
[ 707-07-3 ]
[ 182803-49-2 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7309 - 7315

11
[ 707-07-3 ]
[ 21048-31-7 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 13547 - 13550
[2]Journal of labelled compounds and radiopharmaceuticals,2000,vol. 43,p. 121 - 126

12
[ 132201-32-2 ]
[ 707-07-3 ]
[ 146848-91-1 ]

Reference： [1]Phytochemistry,2001,vol. 58,p. 775 - 787
[2]Polish Journal of Chemistry,2004,vol. 78,p. 89 - 108

13
[ 707-07-3 ]
[ 5098-11-3 ]
methyl N-(4-cyano-1-imidazol-5-yl)benzimidate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3703 - 3708

14
[ 22158-41-4 ]
[ 707-07-3 ]
[ 63388-44-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With pyridinium p-toluenesulfonate; at 90℃; for 2h;	2-phenylnaphtho[2,3-d]oxazole-4,9-dione (A) Intermediate 3 (500 mg, 1.0 eq), trimethylorthobenzoate (3.6 mL, 8.0 eq) and PPTS (66 mg, 0.1 eq) were combined and heated at 90 C. (oil bath) for 2 hours at which point LC-MS analysis indicated complete consumption of starting material. The reaction mixture was diluted with Et2O and the resulting yellow ppt collected and washed with Et2O and EtOAc and dried to yield desired product (472 mg, 65%) as a bright yellow fluffy solid. 1H NMR (400 MHz, CDCl3): delta 7.53-7.62 (3H, M), 7.81 (2H, dd, J=3.5, 5.9), 8.25 (1H, dd, J=3.3, 5.7), 8.29 (1H, dd, J=3.1, 5.9), 8.31-8.34 (2H, M). LRMS (M+H)+: 276.19.

Reference： [1]Heterocyclic Communications,2002,vol. 8,p. 199 - 204
[2]Patent: US9725425,2017,B1 .Location in patent: Page/Page column 104; 105

15
[ 4943-86-6 ]
[ 707-07-3 ]
[ 19857-35-3 ]

Reference： [1]Journal of Chemical Research,2004,p. 570 - 572

16
[ 34813-49-5 ]
[ 707-07-3 ]
methyl N-(tert-butylsulfonyl)benzimidate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 648 - 657

17
[ 87-89-8 ]
[ 707-07-3 ]
myo-inositol 1,3,5-orthobenzoate [ No CAS ]

Reference： [1]Chemical Communications,2006,p. 2989 - 2991
[2]Tetrahedron Letters,2007,vol. 48,p. 1923 - 1926
[3]RSC Advances,2013,vol. 3,p. 7321 - 7329

18
[ 631090-16-9 ]
[ 707-07-3 ]
(2S,3R)-2-azido-1-O-benzoylpent-4-ene-1,3-diol [ No CAS ]
[ 631090-24-9 ]

Yield	Reaction Conditions	Operation in experiment
50%; 44.6%		To a solution containing diol 2 (7.1 g, 49.6 mmol) and trimethyl orthobenzoate (15 ml, 87.3 mmol) in chloroform (150 ml), was added camphor sulphonic acid (500 mg), and the reaction mixture was concentrated to 1/3 of its original volume using a rotavap; TLC revealed that the reaction is not finished, so more chloroform (-100 ml) was added to the mixture, and the solution was concentrated to its 1/3 volume again. This cycle was repeated until TLC indicates the complete consumption of starting material (usually 3-4 cycle needed). Et3N (1 ml) was added to the reaction mixture and the solvent was removed completely; the resulting syrup was treated with a 20% [ACOH-H20] solution (140 ml). After 30 min, the reaction was concentrated to dryness. The syrupy mixture was purified by column chromatography on silica gel using 5% AcOEt-toluene to afford 20 (6.17 g, 50%) and 21 (5.47 g, 44. [6%).'H] NMR (CDCl3, 600 MHz) for 20: [88.] 03 (m, 2H, Bz), 7.55 (m, [1H,] Bz), 7.43 (m, 2H, Bz), 5.94 (ddd, 1H, [J6.] 4,10. 6,17. 0 Hz, H-4), 5.41 (ddd, 1H, J 1.3, 1.3, 17.2 Hz, [H-5_TRANS),] 5.31 (ddd, 1H, J 1.3, 1.3, 10.4 Hz, H-5_cis), 4.57 (dd, [J3.] 7,11. 9 Hz, [H-LA),] 4.42 (dd, 1H, [J 7.] 7,11. 7 Hz, H-lb), 4.28 (m, 1H, H-3), 3.80 (ddd, 1H, J 3.5, 5.3, 7.7 Hz, [H-2). H] NMR (CDC13,600 MHz) for 21: [88.] 05 (m, 2H, Bz), 7.57 (m, 1H, Bz), 7.44 (m, 2H, Bz), 5.97 (ddd, [1H,] J 7.0, 10.6, 17.4 Hz, H-4), 5.66 (m, 1H, H-3), 5.48 (ddd, 1H, J 1.1, 1.1, 17.2 Hz, H- 5trans), 5.31 (ddd, [1H,] [J0.] 9,0. 9,10. 6 Hz, H-5_cis), 3. 83 (ddd, 1H, [J4.] 4,7. 1,9. 2 Hz, H-2), 3. 78 (dd, [J3.] 7,11. 9 Hz, [H-LA),] 4.42 (dd, 1H, [J7.] 7,11. 7 Hz, H-lb),

Reference： [1]Patent: WO2003/101937,2003,A1 .Location in patent: Page 20-22; 42-43

19
[ 135582-93-3 ]
[ 707-07-3 ]
[ 641617-06-3 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In dichloromethane; at 20℃; for 1h;	(EXAMPLE 6) Preparation of (2R/S, 4S)-4-[(N-benzyloxycarbonyl)aminomethyl]-2-methoxy-2-phenyl-1,3-dioxolane [Preparation of Compound (4)] In 5 ml of methylene chloride, 1.00 g (4.44 mmol) of (S)-1-(N-benzyloxycarbonyl)amino-2,3-propanediol was dissolved, and 1.05 g (5.68 mmol, 130 mol%) of trimethyl orthobenzoate and 2.63 mg (0.0138 mmol, 0.31 mol%) of p-toluenesulfonic acid monohydrate were added'to the resultant solution, followed by stirring at room temperature for 1 hour. After the solvent was distilled off under reduced pressure, the residue was dried in vacuum to produce 1.38 g of (2R/S, 4S)-4-[(N-benzyloxycarbonyl)aminomethyl]-2-methoxy-2-phenyl-1,3-dioxolane as a colorless oily diastereomer mixture. HPLC retention time: 20.6 min., 23.8 min.1H NMR (400 MHz, CDCl3) delta 7.58-7.54 (2H, m), 7.44-7.34 (8H, m), 5.45, 4.96 (1H, bs×2), 5.13, 5.09 (2H, s×2), 4.58-4.59, 4.39-4.30 (1H, m×2), 4.32, 4.22 (1H, t×2, J=7.6Hz), 3.89-3.86 (1H, m), 3.50-3.47 (1H, m), 3.35-3.29 (1H, m), 3.21, 3.20 (3H, s×2)

Reference： [1]Patent: EP1553093,2005,A1 .Location in patent: Page/Page column 13

20
[ 707-07-3 ]
[ 220805-65-2 ]
C₁₃H₁₅BrO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		To a stirred solution of 18 (2.92 g, 18 mmol) in dry dichloromethane (30 mL), trimethyl orthobenzoate (4.33 mL, 25.2 mmol) and BF3.diethyl ether (0.11 mL, 0.9 nmol) were added sequentially at RT and stirred for 2 hrs. More trimethly orthobenzoate (1.86 mL, 0.0108 mol) and BF3.diethyl ether (0.11 mL, 0.8 mmol) were added and stirring was continued for 1 hr. The solvent was removed under reduced pressure and the residue was dried over high vacuum. The resulting yellow oil was dissolved in dry dichloromethane (30 mL), cool to 0 C., added with freshly distilled acetyl bromide (1.4 mL, 18.9 mmol), and stirred for 2 hrs. More acetyl bromide (0.07 mL, 0.9 mmol) was added at 0 C. and stirring was continued at RT for 12 hrs. The reaction mixture was treated with saturated aqueous NaHCO3 solution (60 mL) and stirred vigorously for 10 minutes. The mixture was extracted with EtOAc (3×15 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to yield crude 19 (6 g, 100%) as a yellow pale oil, which was taken into next step without further purification: Rf 0.7, EtOAc/petroleum ether (1.5:8.5, v/v).

Reference： [1]Patent: US2005/203162,2005,A1 .Location in patent: Page/Page column 19

21
[ 83808-20-2 ]
[ 707-07-3 ]
[ 108263-83-8 ]

Yield	Reaction Conditions	Operation in experiment
52%	acetic acid; at 120℃; for 1.5h;	Step 3: l-cvclohexvl-2-phenvl-l,5-dihydro-4/f-imidazol-4-one; JV2-cyclohexylglycinamide (from Step 2) was treated with triethylorthobenzoate (1.03 eq.) and catalytic amount of glacial AcOH. The reaction mixture was heated at 120C for 1.5 h then cooled to RT and concentrated. Acetone was added to the residue and the resulting precipitate was filtered to afford the title compound (52%) as a solid. .H NMR (300 MHz, CDC13, 300 K) 8 1.1-1.3 (m, 3H), 1.5-1.9 (m, 7H), 3.8-3.9 (m, 1H), 4.0 (s, 2H), 7.5-7.6 (m, 5H); MS (ES+) m/z 243 (M+H)+.

Reference： [1]Patent: WO2006/8556,2006,A1 .Location in patent: Page/Page column 16

22
[ 53929-59-2 ]
[ 707-07-3 ]
7-methyl-2-phenyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Raney Ni (1.5 g) is added to a mixture of commercially available nitrogen- containing 4-methyl-3-nitropyridin-2-amine x220 (4.0 g, 26.1 mmol) in methanol (150 ml), and the obtained reaction mixture is hydrogenated in the Parr apparatus at the hydrogen pressure 3 atm until the total conversion of compound x220 is attained for approximately 1.5-2 h. The catalyst is separated by filtration, the filtrate is washed with methanol, and the alcohol solution is evaporated to dryness. The residue is dissolved in sulfolane (10 ml), then PhC(OMe)3 (5.7 g, 1.2 eq, 31.3 mmol) and PTSA (0.3 g) are added, and an air reflux condenser is mounted. The apparatus is argon-blown, and the obtained reaction mixture is heated to 165 0C under vigorous stirring for 10 h. Water (100 ml), saturated aqueous NaHCC>3 (5 ml), and hexane (50 ml) are added to the reaction mixture. The obtained suspension is stirred for 5 min, and the residue is separated by filtration. The residue is washed with water (50 ml) and hexane (100 ml), and vacuum-dried over P2O5 to a constant weight at 45 0C to give 7-methyl-2-phenyl-3H-imidazo[4,5-b]pyridine x221 (2.2 g).Yield: 40 %. LC-MS (MH+): 210.

Reference： [1]Patent: WO2006/128692,2006,A2 .Location in patent: Page/Page column 147

23
[ 952575-89-2 ]
[ 707-07-3 ]
[ 952575-73-4 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6148 - 6151

24
[ 420-04-2 ]
[ 707-07-3 ]
[ 6041-23-2 ]

Yield	Reaction Conditions	Operation in experiment
79.2%	With acetic anhydride; at 135℃; for 0.75h;	Preparation of N-(5-phenyI-l,2,4-oxadiazol-3-yl)benzamide (Example No. 11); Step A. Preparation of (Z)-methyl N-cyanobenzimidate; To a mixture of (trimethoxymethyl)benzene (3.44 mL, 20 mmol) and cyanamide (0.842 g, 20 mmol) was added acetic anhydride (3.78 mL, 40 mmol). The mixture was heated to 135C for 45 min. Acetic acid produced in the reaction was removed under reduced pressure. The residue was purified with flash chromatography with 0 - 40% ethyl acetate/heptane over 20 minutes, then kept 40% ethyl acetate/heptane for 5 minutes to give (Z)-methyl N-cyanobenzimidate colorless oil (2.54 g, 79.2% yield). 1H NMR (400 MHz, CDCl3 ) delta 8.00-7.95 (m, 2H), 7.76-7.70 (m, IH), 7.66-7.60 (m, 2H), 4.03 (m, 3H).

Reference： [1]Patent: WO2009/11850,2009,A2 .Location in patent: Page/Page column 163

25
[ 615-43-0 ]
[ 707-07-3 ]
[ 1027223-95-5 ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1974 - 1978
[2]Organic Letters,2008,vol. 10,p. 1967 - 1970
[3]Journal of Organic Chemistry,2013,vol. 78,p. 4708 - 4718

26
[ 1160293-25-3 ]
[ 707-07-3 ]
[ 1160293-24-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With acetic anhydride; at 124℃; for 6h;	At room temperature, 20g (74.9mmol) methyl 1-(chloroacetyl)-2-oxoindolin-6-ylcarboxylate was dissolved in 50 ml of acetic anhydride. The mixture is heated at 124 C. Add dropwise 27.28g (149.8mmol) trimethyl orthobenzoate. React for 6h in the open to distill off the volatile parts of the reaction mixture. After the reaction, cooling to room temperature, precipitated crystal. turns on lathe does solvent, using 500 ml DCM (dichloromethane) dissolving the residue, added to the 1.5L in petroleum ether, to separate out the solid, room temperature stirring 3h, ice-bath 1h, filtered to obtain yellow solid 27.4g, the target compound, the yield is 95%.
87.3 - 91.7%	With acetic anhydride; In toluene; at 20 - 104℃; for 3.66667 - 4h;Heating / reflux;Product distribution / selectivity;	Method 1Methyl-1-(chloroacetyl)-2-oxoindoline-6-carboxylate (12,0 g; 0,045 mol) is suspended in toluene (60 ml) at ambient temperature. Acetic anhydride (16,2 g; 0,157 mol) is added to this suspension. The mixture is heated to not less than 104 C and trimethyl orthobenzoate (20,0 g; 0,108 mol) is added within 60 min. During the addition period and subsequent stirring at the same temperature for 3 h, volatile parts of the reaction mixture are distilled off. The concentration of the reaction mixture is kept constant by replacement of the distilled part by toluene (40 ml). The mixture is cooled down to 5 C, stirred for an additional 1 h and filtrated. The solid is subsequently washed with toluene (14 ml) and with a mixture of toluene (8 ml) and ethyl acetate (8 ml). After drying, 16,3 g (91 ,7 %) of the "chlorenol" compound are isolated as slightly yellow crystals. 1H-NMR (500 MHz, DMSO-de) delta: 8,73 (d, J = 1 ,5 Hz, 1 H, 6-H); 8,09 (d, J = 8,0 Hz, 1 H, 9-H); 7,90 (dd, J = 8,1 ; 1 ,5 Hz, 1 H, 8-H); 7,61 - 7,48 (m, 5 H, 21 -H, 22-H, 23-H, 24-H, 25-H); 4,85 (s, 2 H, 18-H2); 3,89 (s, 3 H, 27-H3); 3,78 (s, 3 H, 15-H3). 13C- NMR (126 MHz, DMSO-d6) delta: 165,9 (C-2 + C16); 103,9 (C-3); 127,4; 128,6; 130,0; 135,4 (C-4 + C-5 + C-7 + C-20); 115,1 (C-6); 126,1 (C-8); 122,5 (C-9); 166,7 (C-10); 173,4 (C-13); 58,4 (C-15); 46,4 (C-18); 128,6 (C-21 + C-22 + C- 24 + C-25); 130,5 (C-23); 52,2 (C-27). MS: m/z 386 (M+H)+. Anal, calcd. for C20Hi6CINO5: C, 62.27; H, 4.18; Cl, 9.19; N, 3.63. Found: C, 62.21 ; H, 4.03; Cl, 8.99; N, 3.52. Method 3Methyl-1-(chloroacetyl)-2-oxoindoline-6-carboxylate (12,0 g; 0,045 mol) is suspended in toluene (60 ml) at ambient temperature. Acetic anhydride (16,2 g; 0,157 mol) is added to this suspension. The mixture is heated to reflux, trimethyl orthobenzoate (20,0 g; 0,108 mol) is added within 40 min and heating is maintained for an additional 3 h. The mixture is cooled down to 0 C and the mother liquor is separated. The solid is subsequently washed with toluene (14 ml) and a mixture of toluene (8 ml) and ethyl acetate (8 ml). After drying 15,3 g (87,3 %) of the "chlorenol" compound are isolated as fawn crystals.
87.3 - 91.7%	With acetic anhydride; In toluene; at 104℃; for 3.66667 - 4h;Heating / reflux;Product distribution / selectivity;	Example 3:; Synthesis of the "chlorenol" (methyl-1-(chloroacetyl)-3- [methoxy(phenyl)methylene]-2-oxoindoline-6-carboxylate)"chlorimide" " chlorenol"Method 1 Methyl-1-(chloroacetyl)-2-oxoindoline-6-carboxylate (12,0 g; 0,045 mol) is suspended in toluene (60 ml) at ambient temperature. Acetic anhydride (16,2 g; 0,157 mol) is added to this suspension. The mixture is heated to not less than 104 0C and trimethyl orthobenzoate (20,0 g; 0,108 mol) is added within 60 min. During the addition period and subsequent stirring at the same temperature for 3 h, volatile parts of the reaction mixture are distilled off. The concentration of the reaction mixture is kept constant by replacement of the distilled part by toluene (40 ml). The mixture is cooled down to 5 0C, stirred for 1 h and filtrated. The solid is subsequently washed with toluene (14 ml) and with a mixture of toluene (8 ml) and ethyl acetate (8 ml). After drying, 16,3 g (91 ,7 %) of the "chlorenol" compound are isolated as slightly yellow crystals. 1H-NMR (500 MHz, DMSO-de) delta: 8,73 (d, J = 1 ,5 Hz, 1 H, 6-H); 8,09 (d, J = 8,0 Hz, 1 H, 9-H); 7,90 (dd, J = 8,1 ; 1 ,5 Hz, 1 H, 8-H); 7,61 - 7,48 (m, 5 H, 21 -H, 22-H, 23-H, 24-H, 25- H); 4,85 (s, 2 H, 18-H2); 3,89 (s, 3 H, 27-H3); 3,78 (s, 3 H, 15-H3). 13C-NMR (126 MHz, DMSO-de) delta: 165,9 (C-2 + C16); 103,9 (C-3); 127,4; 128,6; 130,0; 135,4 (C-4 + C-5 + C-7 + C-20); 1 15,1 (C-6); 126,1 (C-8); 122,5 (C-9); 166,7 (C-10);173.4 (C-13); 58,4 (C-15); 46,4 (C-18); 128,6 (C-21 + C-22 + C-24 + C-25);130.5 (C-23); 52,2 (C-27). MS: m/z 386 (M+H)+. Anal, calcd. for C20Hi6CINO5: C, 62.27; H, 4.18; Cl, 9.19; N, 3.63. Found: C, 62.21 ; H, 4.03; Cl, 8.99; N, 3.52.; Method 3Methyl-1-(chloroacetyl)-2-oxoindoline-6-carboxylate (12,0 g; 0,045 mol) is suspended in toluene (60 ml) at ambient temperature. Acetic anhydride (16,2 g; 0,157 mol) is added to this suspension. The mixture is heated to reflux, trimethyl orthobenzoate (20,0 g; 0,108 mol) is added within 40 min and heating is maintained for 3 h. The mixture is cooled down to 0 0C and the mother liquor is separated. The solid is subsequently washed with toluene (14 ml) and a mixture of toluene (8 ml) and ethyl acetate (8 ml). After drying 15,3 g (87,3 %) of the "chlorenol" compound are isolated as fawn crystals.

81%	With acetic anhydride; In xylene; at 20℃; for 4.66667h;Heating / reflux;Product distribution / selectivity;	Method 2 <n="19"/>Methyl-1-(chloroacetyl)-2-oxoindoline-6-carboxylate (12,0 g; 0,045 mol) is suspended in xylene (60 ml) at ambient temperature. Acetic anhydride (16,2 g; 0,157 mol) is added to this suspension. The mixture is heated to reflux, trimethyl orthobenzoate (20,0 g; 0,108 mol) is added within 40 min and heating is maintained for an additional 4 h. The mixture is cooled down to 0 C and the mother liquor is separated. The solid is subsequently washed with xylene (14 ml) and a mixture of xylene (8 ml) and ethyl acetate (8 ml). After drying 14,3 g (81 ,0 %) of the "chlorenol" compound are isolated as yellow crystals.
81.0%	With acetic anhydride; In xylene; for 4.66667h;Heating / reflux;Product distribution / selectivity;	Method 2; Methyl-1-(chloroacetyl)-2-oxoindoline-6-carboxylate (12,0 g; 0,045 mol) is suspended in xylene (60 ml) at ambient temperature. Acetic anhydride (16,2 g; 0,157 mol) is added to this suspension. The mixture is heated to reflux, trimethyl orthobenzoate (20,0 g; 0,108 mol) is added within 40 min and heating is maintained for 4 h. The mixture is cooled down to 0 0C and the mother liquor is separated. The solid is subsequently washed with xylene (14 ml) and a mixture of xylene (8 ml) and ethyl acetate (8 ml). After drying 14,3 g (81 ,0 %) of the "chlorenol" compound are isolated as yellow crystals.

Reference： [1]Patent: ,2016, .Location in patent: Paragraph 0052; 0071; 0072; 0073
[2]Patent: WO2009/71524,2009,A2 .Location in patent: Page/Page column 17-18; 3; 13
[3]Patent: WO2009/71523,2009,A1 .Location in patent: Page/Page column 4; 19
[4]Patent: WO2009/71524,2009,A2 .Location in patent: Page/Page column 17-18; 3; 13
[5]Patent: WO2009/71523,2009,A1 .Location in patent: Page/Page column 4; 20
[6]Journal of labelled compounds and radiopharmaceuticals,2015,vol. 58,p. 308 - 312

27
[ 394-33-2 ]
[ 707-07-3 ]
5-fluoro-2-phenyl-1,3-benzoxazole [ No CAS ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 8821 - 8831

28
[ 704-14-3 ]
[ 707-07-3 ]
[ 77791-12-9 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 8821 - 8831

29
[ 707-07-3 ]
[ 614-21-1 ]
[ 92-71-7 ]

Reference： [1]Chinese Journal of Chemistry,2012,vol. 30,p. 1464 - 1468
[2]Tetrahedron,2009,vol. 65,p. 8821 - 8831

30
[ 771583-12-1 ]
[ 707-07-3 ]
6-bromo-2-phenylquinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To toluene (200 mL), 5-bromo-2-amino-benzylamine (9.5 g, 47.2 mmol) and trimethyl- benzoic orthoester (8.2 g, 47.2 mmol) were added, followed by p-toulensulfonic acid (1.35 g, 7.1 mmol). The resulting suspension was stirred at reflux for 50 hours. The reaction mixture was cooled at r.t., diluted with AcOEt (150 mL), washed with saturated sodium bicarbonate, then with water. The organic layer was dried and concentrated to provide the intermediate dihydroquinazoline as a light brown solid (8.5 g; 63%). This intermediate is dissolved in DCM (20 mL) at r.t., then MnO2 (5.1 g ) was added. The resulting mixture was stirred at r.t. for 48 hrs, then filtered on celite. The filtrate was concentrated to provide the title product as white solid ( 8.1 g, 95%). Cj4H9BrN2; MW: 285.15; MS m/z: 286 (M+ 1). 1H-NMR (300 MHz, d6-DMSO) ppm: 7.58-7.61 (m, 3H), 8.02 (d, IH), 8.17 (dd, IH), 8.49-8.56(m, 3H), 9.70(s, IH).

Reference： [1]Patent: WO2009/152868,2009,A1 .Location in patent: Page/Page column 25

31
[ 676326-36-6 ]
[ 707-07-3 ]
[ 1168152-07-5 ]

Yield	Reaction Conditions	Operation in experiment
85%		A mixture of methyl 1-acetyl-oxindole-6-carboxylate of formula 3 (7.00 g), toluene (20 ml) and acetanhydride (9.8 ml) was stirred in a flask equipped with a small Vigreux column and adistillation adapter at 110C for 5 mm, producing a turbid orange-red solution. At the temperature of 110C, trimethyl orthobenzoate (12.4 ml) was added dropwise to the reaction mixture, followed by toluene (16 ml), by means of a syringe fitted with a needle reaching into the flask. The bath temperature was slowly increased to slowly distil the produced methyl acetate. After distilling for 4 h, the bath temperature was 125C and the distillate volume was6.5 ml. The reaction mixture was left to stand at 20C for 4 h and the crystallization of the product was completed in 2 h at 10C. The product was filtered off, washed with toluene and finally with a mixture of toluene and ethyl acetate (1: 1). The yield was 8.94 g (85%) of a beige powder
33.99 g	In toluene;Reflux;	Methyl 2-oxindoline-6-carboxylate (20 g, 105 mmol) was charged to the reaction vessel. The vessel was equipped with thermometer, stirrer and condenser. Toluene (100 ml, 5 vol) was added followed by acetic anhydride (90 ml, 954 mmol) and the mixture was heated to reflux (115-118 C ). Reflux was continued for 18 hours and a sample was analyzed by HPLC for methyl 2-oxindoline-6-carboxylate (nmt 2.0 a-%). When the methyl 2-oxindoline-6-carboxylate was consumed 40 ml (2 vol) of solvent was distilled off followed by addition of fresh toluene (40 ml, 2 vol). <strong>[707-07-3]Trimethyl orthobenzoate</strong> (53.9 ml, 314 mmol) was added to the boiling reaction during a couple of minutes maintaining the temperature above 110 C . After the addition was complete distillation began and the temperature of the reaction mixture was above 120 C. Eight volumes (160 ml) of solvents were distilled of after which the reaction temperature was adjusted between 110-115 C. The reflux was continued for two hours and precipitation of methyl (E)-l -acetyl-3 -(methoxy(phenyl)methylene)-2- oxoindoline-6-carboxylate began during the reaction. According to HPLC- chromatogram 93.6 % conversion was achieved. The reaction mixture was allowed to cool to room temperature during 5 hours, and then further cooled to 0 C and stirred for two hours at 0 C. The precipitate was filtered and washed with EtOAc (2 x 20 ml, 2 x 1 vol) and dried in vacuum oven at 60 C for 16 hours to obtain the product (33.99 g, 90.85 %, 98.36 a-%) as tan powder. H NMR (400 MHz, DMSO- d6): delta 8.89 (dd, J= 1.5 Hz, J= 0.6 Hz, 1H), 8.0 (dd, J= 8.0 Hz, J= 1.6 Hz, 1H), 7.94 (dd, J= 8.1 Hz, J= 1.6 Hz, 1H), 7.69-7.53 (m, 3H), 7.48-7.33 (m, 2H), 3.93 (s, 3H), 3.76 (s, 3H), 2.57 (s, 3H).13C NMR (l00 MHz, DMSO-d6 ): delta 171.6, 171.3, 167.3, 167.2, 136.8, 131.0, 130.9, 129.1, 128.8, 128.5, 128.1, 126.5, 122.6, 116.7, 106.3, 57.9, 52.2, 27.0.

Reference： [1]Patent: WO2017/16530,2017,A1 .Location in patent: Page/Page column 7; 8
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 4466 - 4480
[3]Patent: WO2019/97112,2019,A1 .Location in patent: Page/Page column 6-8

32
3'-hydrazinocarbonyl-[1,1']bi[tricyclodecyl]-3-carboxylic acid [ No CAS ]
[ 707-07-3 ]
[ 1206697-65-5 ]

Yield	Reaction Conditions	Operation in experiment
19%	With toluene-4-sulfonic acid; In toluene; at 100℃; for 6h;	Procedure J (described for Example 26, Table 3)3'-(5-Phenyl-ri ,3,4loxadiazol-2-ylH1 ,1 'lbirtricvclordecyll-3-carboxylic acid A mixture of 3'-hydrazinocarbonyl-[1 ,1']bi[tricyclo[decyl]-3-carboxylic acid (60 mg), trimethoxymethyl-benzene (31 mg), and p-toluene-sulfonic acid hydrate (31 mg) in toluene (1 ml.) is stirred at 100 0C for 6 h. After cooling the solution to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and the solvent is evaporated. The residue is purified by HPLC on reversed phase (acetonitrile/water) to afford the title compound. Yield: 14 mg (19% of theory) Mass spectrum (ESI"): 457 [M-H]"

Reference： [1]Patent: WO2010/10174,2010,A1 .Location in patent: Page/Page column 63-64

33
[ 1256917-58-4 ]
[ 707-07-3 ]
[ 1256917-41-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridinium p-toluenesulfonate; In dichloromethane; at 20℃; for 2h;	A lO mL round-bottomed flask was charged with 5 -carbon linked dimer triol (8.2 mg, 0.012 mmol) and trimethylorthobenzoate (6.5 muL, 3 eq, Aldrich 98%) in 1 mL of CH2Cl2. To the reaction mixture was added pyridinium p-toluenesulfonate (PPTS, catalytic amount) at room temperature. The reaction mixture was stirred for 2 hr and then quenched with NaHCCb (aq), extracted with ETOAc, dried over MgS O4 and concentrated. The crude product was purified by column chromatography (EtOAc/Hexane = 1/5) to give 7.4 mg in 80% yield.1H NMR : (400 MHz, Acetone-d6) : 7.58-7.55 (m, 2H), 7.33-7.31 (m, 3H), 5.37 (s, 2H), 4.47-4.38 (m, 3H), 4.32-4.27 (m, IH), 4.03-4.02 (m, IH), 3.67 (dd, J=12 Hz, 8Hz, 2H), 2.65-2.58 (m, IH), 2.54-2.47 (m, IH), 2.29-2.18 (m, 2H), 2.15-2.11 (m, IH), 2.08-2.02 (m, 3H), 2.00-1.97 (m, IH), 1.93-1.84 (m, 4H), 1.82-1.73 (m, 4H), 1.69-1.59 (m, 4H), 1.57-1.53 (m, IH), 1.44-1.37 (m, 4H), 1.34 (s, 3H), 1.31 (s, 3H), 1.25-1.17 (m, 2H), 0.98-0.95 (m, 2H), 0.96 (d, J=4Hz, 3H), 0.93 (d, J=4Hz, 3H), 0.91 (d, J=4Hz, 3H), 0.89 (d, J=4Hz, 3H).13C NMR : (400 MHz, Acetone-d6) : 142.12, 129.23, 128.43, 126.14, 110.61,103.42, 103.16, 90.48, 89.77, 81.67, 81.59, 77.86, 73.99, 72.55, 63.13, 61.51, 54.92, 53.30, 52.95, 45.33, 44.86, 39.45, 39.03, 37.98, 37.86, 37.35, 35.28, 35.18, 32.21, 31.95, 31.60, 31.40, 26.32, 25.60, 25.51, 25.44, 25.38, 20.43, 20.32, 13.32, 12.86.

Reference： [1]Patent: WO2010/135427,2010,A2 .Location in patent: Page/Page column 67

34
[ 1262420-20-1 ]
[ 707-07-3 ]
[ 1262420-40-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With acetic acid; at 70℃; for 3h;	Step A: Methyl 3-amino-2-(2,2-dimethoxyethylamino)benzoate (922 mg, 3.6 mmol) from Step C of Example 13 was stirred in glacial acetic acid (2.5 mL) and(trimethoxymethyl)benzene (2.0 g, 10.9 mmol) at 70 0C for 3 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography (silica gel, 80:20 hexanes/ethyl acetate) to give methyl l-(2,2- dimethoxyethyl)-2-phenyl-lH-benzo[J]imidazole-7-carboxylate as a brown oil (1.0 g, 83%): 1H NMR (500 MHz, CDCl3) delta 7.99 (d, J = 8.0 Hz, I H), 7.95 (d, J= 8.0 Hz, I H), 7.72-7.70 (m, 2H), 7.53-7.51 (m, 3H), 7.33 (t, J = 8.0 Hz, I H), 4.76 (d, J= 5.0 Hz, 2H), 4.24 (t, J= 5.0 Hz, I H), 3.99 (s, 3H), 3.07 (s, 6H); MS (ESI+) m/z 341 (M+H).

Reference： [1]Patent: WO2011/8572,2011,A2 .Location in patent: Page/Page column 88

35
C₃₇H₆₀O₁₁ [ No CAS ]
[ 707-07-3 ]
C₄₄H₆₂O₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridinium p-toluenesulfonate; In dichloromethane; at 20℃; for 2h;	A 10 mLround-botbmed fiaskwas charged with 5-carbon linked dimertriol 5(8.2mg. 0.012 mmol) and trimethylorthobervoate (6.5 p1, 3 eq. Aldrich 98%) in 1 mL of 0H2C12. To the reaction mixture was added pyhdinium p-tnluenesulfonatE (PPTS, 0.4 eq) at room temperature. The reachon mixture was stirred for 2 h and then quenched with NaHCO3(aq), extracted with EtOAc, dried over MgSD4 and concentrated. The crude product was purified by column chromatography (Et1Yc/ Hexane = 1/5) to give 7.4 mg of 6b in 80 % yield.1H NMR : (400 MHz, Acetone-d6) : delta 7.58-7.55 (m, 2H), 7.33-7.31 (m, 3H), 5.37 (s, 2H), 4.47-4.38 (m, 3H), 4.32-4.27 (m, 1H), 4.03-4.02 (m, 1H), 3.67 (dd, J=12 Hz, 8Hz, 2H), 2.65-2.58 (m, 1H), 2.54-2.47 (m, 1H), 2.29-2.18 (m, 2H), 2.15-2.11 (m, 1H), 2.08-2.02 (m, 3H), 2.00-1.97 (m, 1H), 1.93-1.84 (m, 4H), 1.82-1.73 (m, 4H), 1.69-1.59 (m, 4H), 1.57-1.53 (m, 1H), 1.44-1.37 (m, 4H), 1.34 (s, 3H), 1.31 (s, 3H), 1.25-1.17 (m, 2H), 0.98-0.95 (m, 2H), 0.96 (d, J=4Hz, 3H), 0.93 (d, J=4Hz, 3H), 0.91 (d, J=4Hz, 3H), 0.89 (d, J=4Hz, 3H).13C NMR : (400 MHz, Acetone-d6) : delta 142.12, 129.23, 128.43, 126.14, 110.61, 103.42, 103.16, 90.48, 89.77, 81.67, 81.59, 77.86, 73.99, 72.55, 63.13, 61.51, 54.92, 53.30, 52.95, 45.33, 44.86, 39.45, 39.03, 37.98, 37.86, 37.35, 35.28, 35.18, 32.21, 31.95, 31.60, 31.40, 26.32, 25.60, 25.51, 25.44, 25.38, 20.43, 20.32, 13.32, 12.86.[alpha]D25.2 +55.87 (c = 0.35, CHCl3)IR (thin film) 2940, 1450, 1375, 1309, 1101, 1050, 1007, 760 cm-1HRMS(ESI) m/z calcd for C44H62O11 (M+H)+ 767.4292; found 767.4374

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2773 - 2775

36
[ 1329426-42-7 ]
[ 707-07-3 ]
[ 1329426-47-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 6 To a mixture of 16.6 g of compound according to example 2 in toluene (600 ml) trimethyi ortobenzoate (120 ml) and camphenesulphonic acid (4 g) were added. The mixture was stirred vigorously at rt for 3 h, then 80 % acetic acid (160 ml) was added. After further 1 h of stirring the biphasic mixture obtained was separated, the organic phase was diluted with toluene (600 ml), washed with water (800 ml) and sat. NaHC03 (2 x 600 ml), dried, filtered and evaporated. The resulting oil was dropped into 600 ml of heptane and seeded. The white crystalline compound was filtered, washed and dried to yield 1 10.3 g of acceptor (a compound of general formula 6, wherein R\|= Bn, R2= 4-chlorobenzoyl, R3= benzoyl, ORj in beta). [a]D = +17.13 (c = 1 DCM), Mp 156-157 C.
		Example 3 Benzyl 4'-0-benzoyl-2,3,6,2',6'-penta-O-(4-chlorobenzoyl)-P-D-lactosideTo a mixture of 116.6 g of benzyl 2,3,6,2',6'-penta-O-(4-chlorobenzoyl)-P-D-lactoside in toluene (600 ml) trimethyl orthobenzoate (120 ml) and camphenesulphonic acid (4 g) were added. The mixture was stirred vigorously at rt for 3 h, then 80 % acetic acid (160 ml) was added. After further 1 h of stirring the biphasic mixture obtained was separated, the organic phase was diluted with toluene (600 ml), washed with water (800 ml) and sat. NaHC03 (2 x 600 ml), dried, filtered and evaporated. The resulting oil was dropped into 600 ml of heptane and seeded. The white crystalline compound was filtered, washed and dried to yield 110.3 g of product.[
110.3 g	With camphenesulphonic acid; In toluene; at 20℃; for 3h;	To a mixture of 116.6 g of compound according to example 2 in toluene (600 ml) trimethyl ortobenzoate (120 ml) and camphenesulphonic acid (4 g) were added. The mixture was stirred vigorously at rt for 3 h, then 80% acetic acid (160 ml) was added. After further 1 h of stirring the biphasic mixture obtained was separated, the organic phase was diluted with toluene (600 ml), washed with water (800 ml) and sat. NaHCO3 (2×600 ml), dried, filtered and evaporated. The resulting oil was dropped into 600 ml of heptane and seeded. The white crystalline compound was filtered, washed and dried to yield 110.3 g of acceptor (a compound of general formula 6, wherein R1=Bn, R2=4-chlorobenzoyl, R3=benzoyl, OR1 in beta). [alpha]D=+17.13 (c=1 DCM), Mp 156-157 C.

Reference： [1]Patent: WO2011/100980,2011,A1 .Location in patent: Page/Page column 34
[2]Patent: WO2012/155916,2012,A1 .Location in patent: Page/Page column 49
[3]Patent: US8993740,2015,B2 .Location in patent: Page/Page column 28

37
[ 570-24-1 ]
[ 707-07-3 ]
[ 3659-77-6 ]