[ CAS No. 572-09-8 ]

Name: 572-09-8|2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide|98% (stabilized with 1% CaCO3)
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 572-09-8 ]

CAS No. :	572-09-8	MDL No. :	MFCD00063254
Formula :	C₁₄H₁₉BrO₉	Boiling Point :	412°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	411.20	Pubchem ID :	-
Synonyms :

Computed Properties of [ 572-09-8 ]

TPSA :Topological Polar Surface Area	-	H-Bond Acceptor Count :	-
XLogP3 :	-	H-Bond Donor Count :	-
SP3 :	-	Rotatable Bond Count :	-

Safety of [ 572-09-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 572-09-8 ]

Upstream synthesis route of [ 572-09-8 ]
Downstream synthetic route of [ 572-09-8 ]

[ 572-09-8 ] Synthesis Path-Upstream 1~7

1
[ 773-76-2 ]
[ 572-09-8 ]
[ 492-61-5 ]
[ 130-16-5 ]

Reference： [1] Dalton Transactions, 2013, vol. 42, # 6, p. 2023 - 2034

2
[ 572-09-8 ]
[ 138-52-3 ]

Reference： [1] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588

3
[ 160227-12-3 ]
[ 4753-07-5 ]
[ 572-09-8 ]
[ 3068-32-4 ]

Reference： [1] Carbohydrate Research, 1996, vol. 295, p. 41 - 55

4
[ 25878-60-8 ]
[ 572-09-8 ]
[ 3068-32-4 ]

Reference： [1] Chemical Biology and Drug Design, 2012, vol. 80, # 5, p. 647 - 656

5
[ 572-09-8 ]
[ 118-34-3 ]

Reference： [1] Synthesis, 1998, # 2, p. 157 - 161
[2] Chemische Berichte, 1929, vol. 62, p. 2279

6
[ 20675-96-1 ]
[ 572-09-8 ]
[ 118-34-3 ]

Reference： [1] Chemische Berichte, 1955, vol. 88, p. 16,20

7
[ 112-17-4 ]
[ 604-69-3 ]
[ 112-29-8 ]
[ 572-09-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	at 20℃; Irradiation; Green chemistry	General procedure: Bromine (1.5 mmol, 0.08 mL) was added slowly to a magnetic stirring barand perfluorohexanes (4.0 mL) in a test tube (14 mmφ x 105 mm) with a septum and then 1-O-acetylsugar 1a (1 mmol, 392 mg) in ethyl acetate (2.0 mL) wasadded slowly, forming three layers. The test tube was stirring upon irradiationwith 15 W black light (at 352 nm, TOSHIBA EFD15BLB-T) at 30 C. The light source wasplaced away from the test tube. After 23 hours, the bromine layer disappearedand the fluorous layer recovered transparency. The ethyl acetate layer wastaken up with a pipette. Then, additional ethyl acetate (2 mL x 4) was placedon the residual FC-72 layer, followed by decanting off. The combined ethylacetate layer was washed with water (15 mL), aqueous sat. NaHCO₃ (20mL), brine (20 mL) and, dried over Na₂SO₄, andconcentrated. Purification by chromatography on silica gel with hexane/AcOEt = 2/1gave glycosyl bromide 2a (0.91 mmol,374 mg) in 91percent yield

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 52, p. 7124 - 7126

[ 572-09-8 ] Synthesis Path-Downstream 1~7

1
[ 6100-74-9 ]
[ 572-09-8 ]
[ 102761-95-5 ]

Reference： [1]Canadian Journal of Biochemistry and Physiology,1957,vol. 35,p. 161,164, 166

2
[ 939-69-5 ]
[ 572-09-8 ]
[ 131474-31-2 ]

Reference： [1]Carbohydrate Research,1990,vol. 205,p. 225 - 233

3
[ 18362-30-6 ]
[ 572-09-8 ]
[ 159194-03-3 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1994,p. 1697 - 1698

4
[ 42019-78-3 ]
[ 572-09-8 ]
Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-chloro-benzoyl)-phenoxy]-tetrahydro-pyran-4-yl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 898 - 903

5
[ 61439-59-6 ]
[ 572-09-8 ]
C₂₉H₃₄O₁₁ [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2010,vol. 58,p. 1627 - 1629

6
[ 572-09-8 ]
[ 302348-51-2 ]
[(3R,4S,6S)-3,4,5-triacetoxy-6-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy]tetrahydropyran-2-yl]methyl acetate [ No CAS ]
[(2R,3aS,6R,7S)-6,7-diacetoxy-2-methyl-2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy]-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; In dichloromethane; toluene; at -78 - 20℃; for 13.17h;	To the solution of 819 mg [4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl] methanol (3.50 mmol, 1 eq.), 2015 mg l-bromo-2, 3,4, 6-tetra-0-acetyl-a/p-D- mannopyranose (4.90 mmol, 1.4 eq.), 467 mg s-collidine (3.85 mmol, 1.1 eq.) in 100 mL DCM 1708 mg silver trifluoromethanesulfonate (6.65 mmol, 1.9 eq.) in 15 mL toluene was added dropwise at -78 °C and the mixture was stirred at this temperature for 10 minutes. The mixture was let to warm slowly to r.t. (3 hours), then it was stirred for 10 hours. The mixture was filtered through a Celite pad, the filtrate was concentrated. The residue was purified by flash chromatography on silica gel using heptane and ethyl acetate as eluents to give Preparation 4o as first eluted product 1H NMR (500 MHz, DMSO-d6): 7.69 (m, 2H), 7.39 (m, 2H), 5.15-5.10 (m, 3H), 4.96 (d, 1H), 4.71 (d, 1H), 4.57 (d, 1H), 4.15 (dd, 1H), 4.04 (dd, 1H), 3.96 (m, 1H), 2.12-1.91 (s, 12H), 1.29 (s, 12H); and Preparation 4p as later eluted product. 1H NMR (500 MHz, DMSO-d6): 7.63 (m, 2H), 7.31 (m, 2H), 5.68 (d, 1H), 5.32 (dd, 1H), 5.05 (t, 1H), 4.59 (d, lh) 4.54 (dd, 1H), 4.53 (d, 1H), 4.12 (dd, 1H), 4.03 (dd, 1H), 3.94 (m, 1H), 2.01-1.97 (s, 9H), 1.70 (s, 3H), 1.29 (s, 12H)

Reference： [1]Patent: WO2016/207216,2016,A1 .Location in patent: Page/Page column 47; 48

7
[ 16957-70-3 ]
[ 572-09-8 ]
1-O-((E)-2-methylpent-2-enoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With tetraethylammonium bromide; potassium carbonate; In dichloromethane; at 20℃;Molecular sieve;	General procedure: A mixture of glucosyl bromide 1 (1.03 g, 2.5 mmol), acid (5.0 mmol), K2CO3 (0.69 g, 5.0 mmol),TEAB (0.05 g, 0.25 mmol) and 4 A MS (0.25 g) in 35 mL DCM was stirred 24?48 h at room temperature.Next, the insoluble substances, made up of the slightly soluble potassium carboxylate, 4 A MS andother salts, were filtered off. The filtrate was washed with water, and the separated organic layer wasthen washed with 25percent aqueous K2CO3 to removed any remaining potassium carboxylate. After dryingover MgSO4 and concentration in vacuo, the residue was purified via silica gel column chromatographyusing EtOAc/hexane or EtOAc/petroleum ether (1:10 to 1:1) as eluents to yield the desired product.

Reference： [1]Molecules,2017,vol. 22

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[ CAS No. 572-09-8 ]

Quality Control of [ 572-09-8 ]

Related Doc. of [ 572-09-8 ]

Product Details of [ 572-09-8 ]

Computed Properties of [ 572-09-8 ]

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Application In Synthesis of [ 572-09-8 ]

[ 572-09-8 ] Synthesis Path-Upstream 1~7

[ 572-09-8 ] Synthesis Path-Downstream 1~7

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