[ CAS No. 138-52-3 ] {[proInfo.proName]}

Name: 138-52-3|(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(2-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol|98%
Brand: Ambeed
SKU: A190057
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2D 3D

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Quality Control of [ 138-52-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 138-52-3 ]

SDS Specification

Alternatived Products of [ 138-52-3 ]

Product Details of [ 138-52-3 ]

CAS No. :	138-52-3	MDL No. :	MFCD00006590
Formula :	C₁₃H₁₈O₇	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NGFMICBWJRZIBI-UJPOAAIJSA-N
M.W :	286.28	Pubchem ID :	439503
Synonyms :	D-(−)-Salicin;Salicoside;D-(-)-Salicin;NSC 5751	Chemical Name :	(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(2-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triol

Calculated chemistry of [ 138-52-3 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.54
Num. rotatable bonds :	4
Num. H-bond acceptors :	7.0
Num. H-bond donors :	5.0
Molar Refractivity :	66.72
TPSA :	119.61 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.46
Log Po/w (XLOGP3) :	-1.22
Log Po/w (WLOGP) :	-1.79
Log Po/w (MLOGP) :	-1.48
Log Po/w (SILICOS-IT) :	-0.85
Consensus Log Po/w :	-0.78

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.8
Solubility :	44.9 mg/ml ; 0.157 mol/l
Class :	Very soluble
Log S (Ali) :	-0.8
Solubility :	45.7 mg/ml ; 0.16 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.04
Solubility :	259.0 mg/ml ; 0.904 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	4.23

Safety of [ 138-52-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P272-P280-P302+P352-P333+P313-P362+P364-P501	UN#:	N/A
Hazard Statements:	H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 138-52-3 ]

* 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 [ 138-52-3 ]
Downstream synthetic route of [ 138-52-3 ]

[ 138-52-3 ] Synthesis Path-Upstream 1~9

1
[ 16643-37-1 ]
[ 138-52-3 ]

Yield	Reaction Conditions	Operation in experiment
80 mg	With sodium methylate In methanol at 20℃; for 1 h; Inert atmosphere	General procedure: To a solution 2 and the acceptor ArOH (3.0 equiv) in dry DCM (0.1 M) was added afreshly prepared solution of BF3•OEt2 (1.0 equiv., 1M in dry DCM). The solution wasstirred 1 h and followed by TLC (30:70; EtOAc : hexanes). A solution of NaHCO3(aq) wasadded and the mixture was extracted with DCM, washed with brine, dried over Na2SO4,filtered and concentrated in vacuo. The α/β ratio was measured by 1H NMR on the crude.The residue was treated with a freshly prepared solution MeONa (0.25 equiv., 0.5 M inmethanol) in dry methanol (0.3 M). The solution was stirred at r.t. for 1 h andneutralized with Amberlite IR-120 H+, filtered and concentrated in vacuo to give a whitesolid. Quick flash column chromatography (10:90; MeOH:DCM) removed excess of ArOHand led to the β-D anomer, which was recrystallized in hot ethanol.

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

2
[ 29836-40-6 ]
[ 138-52-3 ]

Reference： [1] Journal of Natural Products, 2004, vol. 67, # 4, p. 659 - 663

3
[ 2280-44-6 ]
[ 90-01-7 ]
[ 7724-09-6 ]
[ 138-52-3 ]

Reference： [1] Tetrahedron Asymmetry, 2010, vol. 21, # 16, p. 2060 - 2065

4
[ 604-69-3 ]
[ 138-52-3 ]

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

5
[ 572-09-8 ]
[ 138-52-3 ]

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

6
[ 4336-91-8 ]
[ 138-52-3 ]

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

7
[ 14581-83-0 ]
[ 138-52-3 ]

Reference： [1] Cesko-Slovenska Farmacie, 1956, vol. 5, p. 399[2] Chem.Abstr., 1957, p. 8690

8
[ 89-95-2 ]
[ 57-50-1 ]
[ 7724-09-6 ]
[ 138-52-3 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 4, p. 361 - 365

9
[ 29836-41-7 ]
[ 10316-66-2 ]
[ 138-52-3 ]

Reference： [1] Phytochemistry (Elsevier), 1987, vol. 26, # 5, p. 1361 - 1366

[ 138-52-3 ] Synthesis Path-Downstream 1~64

1
[ 14581-83-0 ]
[ 138-52-3 ]

Reference： [1]Cesko-Slovenska Farmacie,1956,vol. 5,p. 399
Chem.Abstr.,1957,p. 8690

2
[ 138-52-3 ]
[ 7234-31-3 ]

Reference： [1]Journal of the American Chemical Society,1934,vol. 56,p. 2495

3
[ 29836-41-7 ]
[ 10316-66-2 ]
(+)-6-hydroxycyclohexen-2-one [ No CAS ]
[ 138-52-3 ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 1361 - 1366

4
pruyanaside A [ No CAS ]
virgaureoside A [ No CAS ]
[ 138-52-3 ]
[ 10019-60-0 ]

Reference： [1]Phytochemistry,1989,vol. 28,p. 1499 - 1502

5
pruyanaside B [ No CAS ]
[ 108124-75-0 ]
populine [ No CAS ]
henryoside [ No CAS ]
[ 138-52-3 ]

Reference： [1]Phytochemistry,1989,vol. 28,p. 1499 - 1502

6
[ 461-71-2 ]
[ 138-52-3 ]
[ 124781-64-2 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 1851 - 1854

7
[ 57392-44-6 ]
[ 138-52-3 ]
6'-O-mono-butyrylsalicin [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 584

8
[ 1460-57-7 ]
[ 138-52-3 ]
[ 69501-35-5 ]
[ 69501-36-6 ]

Reference： [1]Carbohydrate Research,1980,vol. 87,p. 27 - 34

9
[ 100-52-7 ]
[ 138-52-3 ]
[ 144364-11-4 ]

Reference： [1]Phytochemistry,1992,vol. 31,p. 2909 - 2910

10
[ 822-39-9 ]
[ 138-52-3 ]
(2R,3R,4S,5R,6S)-3,4,5-Tris-([1,3,2]dioxaphospholan-2-yloxy)-2-([1,3,2]dioxaphospholan-2-yloxymethyl)-6-[2-([1,3,2]dioxaphospholan-2-yloxymethyl)-phenoxy]-tetrahydro-pyran [ No CAS ]

Reference： [1]Carbohydrate Research,1991,vol. 220,p. 49 - 61

11
[ 138-52-3 ]
[ 2280-44-6 ]

Reference： [1]Carbohydrate Research,1983,vol. 118,p. 205 - 214

12
[ 138-52-3 ]
[ 7695-70-7 ]

Reference： [1]Synthesis,1999,p. 864 - 872

18
[ 1125-88-8 ]
[ 138-52-3 ]
[ 144364-11-4 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 3277 - 3283

19
[ 77-76-9 ]
[ 138-52-3 ]
[ 346575-75-5 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 3277 - 3283

20
[ 138-52-3 ]
[ 2280-44-6 ]
[ 90-01-7 ]

Reference： [1]Phytochemistry,2001,vol. 58,p. 995 - 1005

21
[ 138-52-3 ]
[ 808770-08-3 ]
[ 808770-15-2 ]
[ 808770-11-8 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 8677 - 8680

22
[ 89-95-2 ]
[ 57-50-1 ]
[ 7724-09-6 ]
[ 138-52-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 361 - 365

23
[ 138-52-3 ]
C₁₃H₁₃S₅O₂₂^(5-)*5Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Procedure for microwave-assisted sulfonation: To a stirred solution of the polyphenol or polyalcohol in MeCN (1 - 5 mL) at RT, Et3N (10 eqv per -OH group) and Me3N:SO3 complex (6 eqv per -OH) were added. The reaction vessel was sealed and micro-waved (CEM Discover synthesizer, Cary, NC) for 30 min at 90 0C. Several reaction tubes were pooled for isolation of the product. The MeCN layer was decanted and pooled, while the residue was washed with MeCN (5 mL) and centrifuged. The combined MeCN layers were concentrated in vacuo. Water (5 mL) was added to the residue and stirred for 10 min. The water layer was concentrated to approximately 2 mL, loaded onto a Sephadex G10 column (160 cm) and chromatographed using water as eluent. Fractions were combined based on capillary electrophoresis profiles, concentrated and re-loaded onto a SP Sephadex C25 column for sodium exchange. Appropriate fractions were pooled, concentrated in vacuo, and lyophilized to obtain a white powder.

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 6754 - 6758
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4467 - 4470

24
[ 29836-40-6 ]
[ 138-52-3 ]

Reference： [1]Journal of Natural Products,2004,vol. 67,p. 659 - 663

25
[ 138-52-3 ]
[ 346575-79-9 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 3277 - 3283

26
[ 138-52-3 ]
[ 346575-78-8 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 3277 - 3283

27
[ 138-52-3 ]
2-(phthalimidomethyl)phenyl 4,6-O-(1-methylethylidene)glucopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 3277 - 3283

28
[ 138-52-3 ]
[ 346575-76-6 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 3277 - 3283

29
[ 138-52-3 ]
Methyl (2-methoxycarbonyl-phenyl β-D-glucopyranosid)uronate [ No CAS ]

Reference： [1]Synthesis,1999,p. 864 - 872

30
[ 138-52-3 ]
[ 144364-14-7 ]

Reference： [1]Phytochemistry,1992,vol. 31,p. 2909 - 2910

31
[ 138-52-3 ]
[ 144364-12-5 ]

Reference： [1]Phytochemistry,1992,vol. 31,p. 2909 - 2910

32
[ 138-52-3 ]
[ 144364-13-6 ]

Reference： [1]Phytochemistry,1992,vol. 31,p. 2909 - 2910

33
[ 138-52-3 ]
[ 529-66-8 ]

Reference： [1]Phytochemistry,1992,vol. 31,p. 2909 - 2910

34
[ 138-52-3 ]
<i>o</i>-tolyl-(<i>O</i>⁶-benzoyl-β-D-glucopyranoside) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1934,vol. 56,p. 2495

35
[ 156-38-7 ]
[ 138-52-3 ]
6-O-p-OH-phenylacetyl-[(2-hydroxymethyl)phenyl]-β-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With immobilized lipase B; In tert-butyl alcohol; at 60℃; for 34.0h;	5 mmol <strong>[138-52-3]D-(-)-salicin</strong> [2-hydroxymethyl)phenyl-delta-D-glucopyranoside], 7.5 mmol p-OH-phenylacetic acid, 4 g molecular sieve, 4 ml t-butanol and 2.5 g immobilized lipase B from Candida antarctica were incubated for 34 hours at 60 C. in a rotating 50 ml round-bottom flask. The reaction was monitored by thin-layer chromatography (silica gel 60 plates with fluorescence indicator; mobile solvent: chloroform/methanol/water 65/15/2 v/v/v; visualization: UV detection and with acetic acid/sulfuric acid/anisaldehyde (100:2:1 v/v/v) immersion reagent). The product was extracted with 20 ml of dichloromethane and purified by column chromatography (silica gel F60; mobile solvent: ethyl acetate/methanol 10/1 v/v). After purification, the yield was 17% (white solid). 13C-NMR (CD3OD): delta (ppm)=41.8 (C-2), 61.0 (C-7), 65.0 (C-6'), 71.5 (C-4'), 74.9 (C-2'), 75.4 (C-5'), 77.8 (C-3'), 103.2 (C-1'), 117.1 (C-6), 123.9 (C-4), 129.4-132.3 (C-2, C-3, C-5; C-4, C-5, C-7, C-8), 136.1 (C-3), 156.0-159.2 (C-1*, C-6), 173.31 (CO).

Reference： [1]Patent: US6750332,2004,B1 .Location in patent: Page column 6

36
[ 138-52-3 ]
[ 501-52-0 ]
6-O-phenylpropionyl-[2-(hydroxymethyl)phenyl]-β-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With immobilized lipase B; In tert-butyl alcohol; at 60℃; for 34.0h;	5 mmol <strong>[138-52-3]D-(-)-salicin</strong> [2-hydroxymethyl)phenyl-beta-D-glucopyranoside], 7.5 mmol phenylpropionic acid, 4 g molecular sieve, 4 ml t-butanol and 2.5 g immobilized lipase B from Candida antarctica were incubated for 34 hours at 60 C. in a rotating 50 ml round-bottom flask. The reaction was monitored by thin-layer chromatography (silica gel 60 plates with fluorescence indicator; mobile solvent: chloroform/methanol/water 65/15/2 v/v/v; visualization: UV detection and with acetic acid/sulfuric acid/anisaldehyde (100:2:1 v/v/v) immersion reagent). The product was extracted with 20 ml of dichloromethane and purified by column chromatography (silica gel F60; mobile solvent: ethyl acetate/methanol 10/1 v/v). After purification, the yield was 32% (white solid). 13C-NMR (CD3OD): delta (ppm)=30.9 (C-2), 38.7 (C-3), 61.6 (C-7), 65.2 (C-6'), 72.2 (C-4'), 75.6 (C-2'), 76.1 (C-5'), 78.4 (C-3'), 103.7 (C-1'), 117.6 (C-6), 124.5 (C-4), 127.6 (C-7), 130.1-131.0 (C-3, C-5, C-5, C-6, C-8, C-9), 132.8 (C-2), 143.4 (C-4), 157.5 (C-1'), 175.2 (C'O).

Reference： [1]Patent: US6750332,2004,B1 .Location in patent: Page column 5; 6

37
[ 112-39-0 ]
[ 138-52-3 ]
6-O-palmitoyl-[2-(hydroxymethyl)phenyl]-β-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With immobilized lipase B; In acetone; at 40℃; for 48.0h;	In a two-necked flask surmounted by a Soxhlet extractor (filled with activated molecular sieve), 0.5 g of immobilized Candida antarctica B lipase (SP 435, manufacturer Novo Nordisk) was added to 5 mmol <strong>[138-52-3]D-(-)-salicin</strong> ([2-(hydroxymethyl)phenyl]-beta-D-glucopyranoside) and 5 mmol palmitic acid methyl ester in 50 ml acetone, followed by heating with stirring (magnetic stirrer, 200 r.p.m.) under reduced pressure for 48 h to 40 C. The progress of the reaction was followed by thin-layer chromatography. After the end of the reaction, 14 g warm acetone (ca. 50 C.) were added and the mixture was filtered at 50 C. The filtrate was cooled to -10 C. and the product precipitated was isolated in a yield of 53% by filtration. 13C-NMR (CD3OD): delta (ppm)=14.47 (C-16), 23.74 (C-15), 26.00 (C-3), 30.22-30.80 (C-4-C-13), 33.08 (C-14), 35.03 (C-2), 60.98 (C-7), 64.59 (C-6'), 71.64 (C-4'), 74.96 (C-2'), 75.49 (C-5'), 77.82 (C-3'), 103.22 (C-1'), 117.07 (C-6), 123.82 (C-4), 129.78-132.34 (C-2, C-3, C-5), 156.98 (C-1*), 175.23 (CO). Anal. calculated for C29H48O8 (524.69): C, 66.39; H, 9.22. Found: C, 67.88; H, 9.41.

Reference： [1]Patent: US6750332,2004,B1 .Location in patent: Page column 7

38
[ 138-52-3 ]
[ 57-50-1 ]
[ 1190089-79-2 ]
[ 1190089-80-5 ]

Reference： [1]Carbohydrate Research,2009,vol. 344,p. 1612 - 1619
[2]Carbohydrate Research,2009,vol. 344,p. 1612 - 1619

39
[ 2280-44-6 ]
[ 90-01-7 ]
[ 7724-09-6 ]
[ 138-52-3 ]

Reference： [1]Tetrahedron Asymmetry,2010,vol. 21,p. 2060 - 2065

40
[ 138-52-3 ]
[ 50-99-7 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2011,vol. 59,p. 1954 - 1961

41
[ 138-52-3 ]
[ 50-99-7 ]
[ 90-01-7 ]

Reference： [1]Process Biochemistry,2012,vol. 47,p. 127 - 132

42
[ 138-52-3 ]
[ 90-01-7 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2013,vol. 61,p. 931 - 938

43
[ 138-52-3 ]
[ 3046-82-0 ]
C₄₁H₄₄O₁₆ [ No CAS ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2013,vol. 51,p. 2483 - 2494

44
[ 90-02-8 ]
[ 138-52-3 ]
2''-[(2'-bromoisobutyryloxy)methyl]phenyl 2,3-di-O-(2'-bromoisobutyryl)-4,6-O-(2'-bromoisobutyryloxy)salicylidene-β-D-glucopyranoside [ No CAS ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2013,vol. 51,p. 2483 - 2494

45
[ 90-02-8 ]
[ 138-52-3 ]
2'-(hydroxymethyl)phenyl 4,6-O-salicylidene-β-D-glucopyranoside [ No CAS ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2013,vol. 51,p. 2483 - 2494

46
[ 623-27-8 ]
[ 138-52-3 ]
4,6:4',6'-O-terephtalidenebis[2''-(hydroxymethyl)phenyl-β-D-glucopyranoside] [ No CAS ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2013,vol. 51,p. 2483 - 2494

47
[ 138-52-3 ]
tapioca starch [ No CAS ]
[ 1190089-79-2 ]
[ 1190089-80-5 ]
salicin-α-D-maltotriopyranoside [ No CAS ]

Reference： [1]Carbohydrate Research,2016,vol. 432,p. 55 - 61

48
[ 16643-37-1 ]
[ 138-52-3 ]

Yield	Reaction Conditions	Operation in experiment
80 mg	With sodium methylate; In methanol; at 20℃; for 1.0h;Inert atmosphere;	General procedure: To a solution 2 and the acceptor ArOH (3.0 equiv) in dry DCM (0.1 M) was added afreshly prepared solution of BF3?OEt2 (1.0 equiv., 1M in dry DCM). The solution wasstirred 1 h and followed by TLC (30:70; EtOAc : hexanes). A solution of NaHCO3(aq) wasadded and the mixture was extracted with DCM, washed with brine, dried over Na2SO4,filtered and concentrated in vacuo. The alpha/beta ratio was measured by 1H NMR on the crude.The residue was treated with a freshly prepared solution MeONa (0.25 equiv., 0.5 M inmethanol) in dry methanol (0.3 M). The solution was stirred at r.t. for 1 h andneutralized with Amberlite IR-120 H+, filtered and concentrated in vacuo to give a whitesolid. Quick flash column chromatography (10:90; MeOH:DCM) removed excess of ArOHand led to the beta-D anomer, which was recrystallized in hot ethanol.

Reference： [1]Synthesis,2016,vol. 48,p. 3575 - 3588

49
[ 604-69-3 ]
[ 138-52-3 ]

Reference： [1]Synthesis,2016,vol. 48,p. 3575 - 3588

50
[ 572-09-8 ]
[ 138-52-3 ]

Reference： [1]Synthesis,2016,vol. 48,p. 3575 - 3588

51
[ 4336-91-8 ]
[ 138-52-3 ]

Reference： [1]Synthesis,2016,vol. 48,p. 3575 - 3588

52
[ 138-52-3 ]
[ 492-61-5 ]
[ 90-01-7 ]

Reference： [1]International Journal of Biological Macromolecules,2018,vol. 119,p. 462 - 469

53
2-(chloromethyl)phenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside [ No CAS ]
[ 138-52-3 ]

Reference： [1]Journal of Natural Products,2020,vol. 83,p. 888 - 893

54
2-(chloromethyl)phenyl-2-O-acetyl-β-D-glucopyranoside [ No CAS ]
[ 138-52-3 ]

Reference： [1]Journal of Natural Products,2020,vol. 83,p. 888 - 893

55
2-(hydroxymethyl)phenyl-2-O-acetyl-β-D-glucopyranoside [ No CAS ]
[ 138-52-3 ]

Reference： [1]Journal of Natural Products,2020,vol. 83,p. 888 - 893

56
[ 19764-02-4 ]
[ 138-52-3 ]

Reference： [1]Journal of Natural Products,2020,vol. 83,p. 888 - 893

57
[ 5346-66-7 ]
[ 138-52-3 ]

Reference： [1]Journal of Natural Products,2020,vol. 83,p. 888 - 893
[2]Journal of Natural Products,2020,vol. 83,p. 888 - 893

58
[ 60523-66-2 ]
[ 138-52-3 ]

Reference： [1]Journal of Natural Products,2020,vol. 83,p. 888 - 893
[2]Journal of Natural Products,2020,vol. 83,p. 888 - 893

59
[ 138-52-3 ]
C₃₅H₃₅O₁₂S₂⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Reference： [1]Patent: WO2020/94673,2020,A1

60
[ 138-52-3 ]
fluorosalicin pentaacetate [ No CAS ]

Reference： [1]Patent: WO2020/94673,2020,A1

61
[ 138-52-3 ]
C₂₄H₂₇F₃O₁₂ [ No CAS ]

Reference： [1]Patent: WO2020/94673,2020,A1

62
[ 138-52-3 ]
C₃₅H₃₁F₄O₁₂S₂⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Reference： [1]Patent: WO2020/94673,2020,A1

63
[ 138-52-3 ]
methoxyphenylsalicin pentaacetate [ No CAS ]

Reference： [1]Patent: WO2020/94673,2020,A1

64
[ 108-24-7 ]
[ 138-52-3 ]
[ 16643-37-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In 1,4-dioxane; at 60℃; for 16.0h;	Under an ambient atmosphere, a 250 ml roundbottom flask was charged sequentially with salicine (10.0 g, 35 mmol, 1.0 equiv.), K2C03(24.0 g, 0.18 mol, 2.0 equiv.), and dioxane (140 ml, c = 0.25 M). Acetic anhydride (33.1 ml, 36 g, 0.35 mol, 10 equiv.) was added in one portion to the reaction mixture. The colorless suspension was stirred at 60 C for 16 h before the reaction mixture was concentrated under reduced pressure, diluted with EtOAc (150 ml), and washed with water (ca. 250 ml). The mixture was poured into a separatory funnel, and the layers were separated. The ethylacetate layer was dried over Na2S04, filtered, and the solvent was removed under reduced pressure. The crude product was recrystallized from EtOAc / /- hexane (1 :1 , ca. 100 ml). The crystals were washed with pentane (ca. 50 ml) and dried in vacuo to afford 16.5 g (95 %) of 5a as colorless crystals. NMR Spectroscopy:1H NMR (500 MHz, CDCI3, 298 K, d): 7.32 (dd, J = 7.8 Hz, 1.7 Hz, 1 H), 7.27 - 7.23 (m, 1 H), 7.08 - 7.04 (m, 2H), 5.31 - 5.25 (m, 2H), 5.19 - 5.12 (m, 1 H), 5.09 (d, J = 12.9 Hz, 1 H), 5.06 (d, J = 7.5 Hz, 1 H), 5.02 (d, J = 12.9 Hz, 1 H), 4.26 (dd, J = 12.3 Hz, 5.3 Hz, 1 H), 4.16 (dd, J = 12.3 Hz, 2.5 Hz, 1 H), 3.84 (ddd, J = 10.0 Hz, 5.3 Hz, 2.5 Hz, 1 H), 2.06 (s, 6H), 2.04 (s, 3H), 2.02 (s, 3H), 2.01 (s, 3H).13C {1H} NMR (126 MHz, CDCI3, 298 K, d): 170.7, 170.5, 170.2, 169.4, 169.3, 154.6, 129.6, 129.5, 126.3, 123.6, 1 15.9, 99.4, 72.7, 72.0, 71.0, 68.4, 61.9, 61.1 , 21 .0, 20.7, 20.6 (3 C- atoms).HRMS-ESI(m/z) calc?d for C23H280i2Na+[M+Na]+, 519.147580; found 519.147299; deviation: 0.5 ppm.

Reference： [1]Patent: WO2020/94673,2020,A1 .Location in patent: Page/Page column 31; 32

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[ CAS No. 138-52-3 ] {[proInfo.proName]}

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[ 138-52-3 ] Synthesis Path-Upstream 1~9

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