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Chemical Structure| 48149-72-0 Chemical Structure| 48149-72-0

Structure of Allylα-D-galactopyranoside
CAS No.: 48149-72-0

Chemical Structure| 48149-72-0

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Product Details of [ 48149-72-0 ]

CAS No. :48149-72-0
Formula : C9H16O6
M.W : 220.22
SMILES Code : O[C@H]1[C@@H](OCC=C)O[C@H](CO)[C@H](O)[C@@H]1O
MDL No. :MFCD01320363
InChI Key :XJNKZTHFPGIJNS-NXRLNHOXSA-N
Pubchem ID :2735272

Safety of [ 48149-72-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 48149-72-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 0
Fraction Csp3 0.78
Num. rotatable bonds 4
Num. H-bond acceptors 6.0
Num. H-bond donors 4.0
Molar Refractivity 49.61
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

99.38 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.64
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-1.55
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-2.01
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-1.89
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.19
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-1.0

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

0.04
Solubility 239.0 mg/ml ; 1.08 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.03
Solubility 206.0 mg/ml ; 0.934 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.44
Solubility 6070.0 mg/ml ; 27.5 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-8.74 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

4.46

Application In Synthesis of [ 48149-72-0 ]

* 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 [ 48149-72-0 ]

[ 48149-72-0 ] Synthesis Path-Downstream   1~35

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YieldReaction ConditionsOperation in experiment
88% With toluene-4-sulfonic acid; at 100℃; for 24h; 10241] To a stirred suspension of D-galactose 12 (22.2 g, 123 mmol) in allyl alcohol (250 mE) was added para-toluenesulfonic acid (2.3 g, 12.09 mmol). The mixture was heated to 1000 C. and stirred for 24 h after which it was cooled to r.t. and quenched by the addition of NEt3. The solvent was removed in vacuo and the crude product was co-evaporated twice with toluene and purified by flash column chromatography on silica gel (gradient CH2Cl2/MeOH9: 1 -4: 1). Recrystalization from EtOAc yielded galactoside 13 (22.2 g, 88%) as a white solid.
  • 5
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  • [ 3282-30-2 ]
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  • [ 93619-87-5 ]
  • 9
  • [ 98-88-4 ]
  • [ 48149-72-0 ]
  • allyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside [ No CAS ]
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  • [ 127446-63-3 ]
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  • [ 77-76-9 ]
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  • [ 77-76-9 ]
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  • [ 145012-53-9 ]
  • 14
  • [ 77-76-9 ]
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  • [ 104477-35-2 ]
YieldReaction ConditionsOperation in experiment
With camphor-10-sulfonic acid; at 20℃; for 48h;Inert atmosphere; Allyl- a - D -galactopyranoside 11 (5.00 g, 22.73 mmol,1 equiv) anddry camphorsulfonic acid (0.26 g, 1.14, 5 mol %) were dissolved in2,2-dimethoxypropane under nitrogen atmosphere. The mixturewas stirred for 48 h at room temperature. Triethylamine was thenadded and the mixture was stirred for a further 15 min. The sol-vents were removed under reduced pressure. The residue was thendissolved in methanol/water (10:1) and the resulting solution washeated under reux for 7 h. The solvents were then removed underreduced pressure and the residue was puried using silica gelcolumn chromatography (light petroleum/ethyl acetate 2:3) to givethe desired product (3.93 g, 67%) as a colourless solid.Mp 139 e 140C (lit. Mp 138 e 142C); [ a ]D22148.7 (c 1.0, CHCl3),lit. [ a ]D25131.5 (c 1.0, CHCl3); nmax (neat)/cm13403, 2931, 2359,2340, 1643, 1074, 1039, 871, 688; dH (400 MHz, CDCl3) 2 e OH ex-change, 1.35 (3H, s, CH3),1.51 (3H, s, CH3), 3.75 e 3.85 (2H, m, H-2, H-6A), 3.90 (1H, dd, J6b,5 6.4 Hz, J6b,6a 11.8 Hz, H-6b), 4.07 e 4.10 (2H,m, H-5, e OCHHCHX ] CH2), 4.23 e 4.29 (3H, m, 2CH, e OCHHCHX ]CH2), 4.94 (1H, d, J1,2 3.6 Hz, H-1), 5.23 (1H, dd, JA,B 1.6 Hz,JA,X 10.4 Hz, e OCH2CHX ] CHAHB), 5.29 (1H, dd, JB,A 1.6 Hz,JB,X 15.6 Hz, e OCH2CHX ] CHAHB), 5.85 e 6.00 (1H, m, e OCH2CHX ]CH2); dC (100 MHz, CDCl3) 25.6 (CH3), 27.8 (CH3), 62.6 (CH2), 68.2(C-3), 68.3 (CH2), 69.6 (C-2), 73.9 (CH), 76.3 (CH), 96.8 (CH), 109.8(C), 117.9 (CH2), 135.6 ( e OCH2CHX ] CH2).
  • 15
  • [ 67-64-1 ]
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  • [ 108-24-7 ]
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  • [ 120095-03-6 ]
  • 18
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  • [ 93619-80-8 ]
YieldReaction ConditionsOperation in experiment
General procedure: Ozone was bubbled through a solution of allyl glycoside 16 (250 mg)in MeOH (75 mL) at -78 C until the solution turned blue (ca. 25 min). The solution was purged under N2 flow to remove the excess of ozone, and dimethyl sulfide (1 mL) was added. After a few minutes, nitrogen was again passed through the solution, which was then allowed to warm to r.t. The solvent was removed under reduced pressure to afford glycosyl aldehydes 29-39 (quant.) as a colorless oil. O-Benzylhydroxylamine hydrochloride (1.1 equiv) was then added to the solution of the corresponding glycosyl aldehydes (10 mg, 1 equiv) in H2O (1 mL). The mixture was stirred at 40 C for 30 min and the final oxime was purified by semipreparative HPLC to obtain the Z/E mixture of neoglycoconjugates 47-58.
  • 19
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  • 20
  • [ 1125-88-8 ]
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  • [ 20746-64-9 ]
YieldReaction ConditionsOperation in experiment
STEP 1 : (4aR,6S,7R,8R,8aR)-6-(allyloxy)-2-phenylhexahydropyrano[3,2- d][1,3]dioxine-7,8-diol Into a 3-L 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed (2R,3R,4S,5R,6S)-2-(hydroxymethyl)- 6-(prop-2-en-1 -yloxy)oxane-3,4,5-triol (80 g, 363.27 mmol, 1.00 equiv), CSA (250 mg), (dimethoxymethyl)benzene (82 g, 538.80 mmol, 1.48 equiv), CHCI3 (1.2 L). The resultant suspension was placed in a preheated oil bath (bath temp. 90 C), and the distillate was collected. After approximately 15 ml was collected, the same volume of CHCb was added. This process was repeated. The reaction progress was monitored by TLC. The resulting mixture was washed with 1x500 ml of water and 1x500 ml of saturated aqueous sodium bicarbonate. The resulting mixture was washed with 1x500 ml of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting residue was washed with PE/EA(20: 1) to yield (4aR,6S,7R,8R,8aR)-2-phenyl-6-(prop-2-en-1 -yloxy)-hexahydro-2H-pyrano[3,2- d][1,3]dioxine-7,8-diol as a white solid. 1 H NMR: (300 MHz, CDCI3): delta 7.54- 7.47(m, 2H), 7.41 -7.34(m, 3H), 5.99-5.86(m, 1H), 5.55(s, 1H), 5.34-5.21 (m, 2H), 5.09(s, 1H), 4.29-4.21 (m, 3H), 4.1 1 -4.05(m, 2H), 3.93(s, 2H), 3.74(s, 1H). LC-MS (ES, m/z): 634.2 [2M+NH4] +
With camphorsulfonic acid; In acetonitrile; for 20h; Small-scale synthesis: To a solution of allyl alpha-D-galactopyranoside (1.0 g, 4.51 mmol) in acetonitrile (25 ml) was added p-methoxybenzaldehyde dimethyl acetal (1.65 g, 9.08 mmol) followed by CSA (105 mg, 0.45 mmol). After 20 h, Et3N (0.1 ml) was added and the solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc three times and the combined organic extracts were washed with brine, dried with Na2S04, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (40 g column, EtOAc/heptane: 0>20%>100%, Teledyne ISCO Combiflash) to yield a white solid.
  • 21
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  • [ 258854-17-0 ]
YieldReaction ConditionsOperation in experiment
83% With pyridine; at 20℃; for 18h;Inert atmosphere; Example 27 Synthesis of allyl 6-O-trityl-alpha-D-galactopyranoside (27*) 1-O-Allyl-galactoside (Org. Lett. 2002, 4, 489) (4 g, 18.2 mmol) was dissolved in pyridine (18 mL). To the solution was added trityl chloride (6.58 g, 23.6 mmol) and the mixture was stirred at r.t. for 18 h after which the solvent was removed in vacuo. The crude product was purified by flash column chromatography on silica gel (CH2Cl2/MeOH = 10:1) to yield pyranoside 27* (7.0 g, 83%) as colorless oil. [alpha]Dr.t. = +60.0 (c = 1, CHCl3); Rf = 0.8 (CH2Cl2/MeOH = 5:1); IR (film) vmax 3402, 2929, 1491, 1449, 1218, 1152, 1070, 1032, 746, 703 cm-1; 1H NMR (400 MHz, CDCl3) delta 7.51-7.18 (m, 15H), 5.99-5.88 (m, 1H), 5.25 (ddq, J = 35.9, 10.4, 1.4 Hz, 2H), 4.95 (d, J = 3.8 Hz, 1 H), 4.25 (ddt, J = 12.8, 5.4, 1.4 Hz, 1H), 4.05 (ddt, J = 12.8, 6.3, 1.3 Hz, 1 H), 3.96 (s, 1 H), 3.89 (t, J = 5.8 Hz, 1 H), 3.81 (d, J = 5.7 Hz, 1 H), 3.75 (d, J = 9.8 Hz, 1H), 3.47 (s, 1 H), 3.43 (dd, J = 9.8, 6.1 Hz, 1 H), 3.32 (dd, J = 9.8, 5.3 Hz, 1 H), 2.86 (d, J = 2.1 Hz, 1 H), 2.71 (d, J = 8.1 Hz, 1 H); 13C NMR (75 MHz, CDCl3) delta 143.8, 133.7, 128.6, 127.8, 127.1, 117.8, 97.5, 86.9, 71.2, 69.8, 69.5, 69.5, 68.5, 63.3; HR ESI Calcd for C25H25O5 [M+Na+]: 485.1935 found: 485.1941.
83% With pyridine; at 20℃; for 18h;Inert atmosphere; Example B.15: Synthesis of allyl 6-O-thtyl-alpha-D-galactopyranoside (27*)1 -O-Allyl-galactoside {Org. Lett. 2002, 4, 489) (4 g, 18.2 mmol) was dissolved in pyridine (18 mL). To the solution was added trityl chloride (6.58 g, 23.6 mmol) and the mixture was stirred at r.t. for 18 h after which the solvent was removed in vacuo. The crude product was purified by flash column chromatography on silica gel (CH2CI2/MeOH = 10:1 ) to yield pyranoside 27* (7.0 g, 83%) as colorless oil. [a]Dr t = +60.0 (c = 1 , CHCI3); Rf = 0.8 (CH2CI2/MeOH = 5:1 ); IR (film) vmax 3402, 2929, 1491 , 1449, 1218, 1 152, 1070, 1032, 746, 703 cm"1; 1H NMR (400 MHz, CDCI3) delta 7.51-7.18 (m, 15H), 5.99-5.88 (m, 1 H), 5.25 (ddq, J = 35.9, 10.4, 1 .4 Hz, 2H), 4.95 (d, J = 3.8 Hz, 1 H), 4.25 (ddt, J = 12.8, 5.4, 1 .4 Hz, 1 H), 4.05 (ddt, J = 12.8, 6.3, 1 .3 Hz, 1 H), 3.96 (s, 1 H), 3.89 (t, J = 5.8 Hz, 1 H), 3.81 (d, J = 5.7 Hz, 1 H), 3.75 (d, J = 9.8 Hz, 1 H), 3.47 (s, 1 H), 3.43 (dd, J = 9.8, 6.1 Hz, 1 H), 3.32 (dd, J = 9.8, 5.3 Hz, 1 H), 2.86 (d, J = 2.1 Hz, 1 H), 2.71 (d, J = 8.1 Hz, 1 H); 13C NMR (75 MHz, CDCI3) delta 143.8, 133.7, 128.6, 127.8, 127.1 , 1 17.8, 97.5, 86.9, 71 .2, 69.8, 69.5, 69.5, 68.5, 63.3; HR ESI Calcd for C25H2505 [M+Na+]: 485.1935 found: 485.1941 .
83% With pyridine; at 20℃; for 18h; 10242] 1-0-Allyl-galactoside 13 (4 g, 18.2 mmol) was dissolved in pyridine (18 mE). To the solution was added trityl chloride (6.58 g, 23.6 mmol) and the mixture was stirred at r.t. for 18 h after which the solvent was removed in vacuo. The crude product was purified by flash column chromatography on silica gel (CH2Cl2/MeOH10: 1) to yield pyranoside 14 (7.0 g, 83%) as colorless oil. [a]Dt+60.0 (c1, CHC13); R1O.8 (CH2Cl2/MeOH5:1); IR (film) vm,x 3402, 2929, 1491,1449,1218,1152,1070, 1032,746,703cm?; ?HNMR (400 MHz, CDC13) oe 7.51-7.18 (m, 15H), 5.99-5.88 (m, 1H), 5.25 (ddq, J35.9, 10.4, 1.4 Hz, 2H), 4.95 (d, J3.8 Hz, 1H), 4.25 (ddt, J12.8, 5.4, 1.4 Hz, 1H), 4.05 (ddt, J12.8, 6.3, 1.3Hz, 1H), 3.96 (s, 1H), 3.89 (t, J5.8 Hz, 1H), 3.81 (d, J5.7Hz, 1H), 3.75 (d, J9.8 Hz, 1H), 3.47 (s, 1H), 3.43 (dd, J9.8,6.1 Hz, 1H), 3.32 (dd, J9.8, 5.3 Hz, 1H), 2.86 (d, J2.1 Hz,1H), 2.71 (d, J8.1 Hz, 1H); ?3C NMR (75 MHz, CDC13) oe143.8, 133.7, 128.6, 127.8, 127.1, 117.8, 97.5, 86.9, 71.2,69.8, 69.5, 69.5, 68.5, 63.3; HR ESI Calcd for C25H2505[M+Na]: 485.1935. found: 485.1941.
  • 23
  • [ 74-96-4 ]
  • [ 48149-72-0 ]
  • allyl-2,3,4,6-tetra-O-ethyl-α-D-galactopyranoside [ No CAS ]
  • 24
  • [ 107-82-4 ]
  • [ 48149-72-0 ]
  • [ 188713-60-2 ]
  • 25
  • [ 48149-72-0 ]
  • [ 74-88-4 ]
  • (2S,3R,4S,5S,6R)-2-Allyloxy-6-hydroxymethyl-4-methoxy-tetrahydro-pyran-3,5-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% For allyl 3-O-methyl-alpha-D-galactopyranoside (15), a micro-wave vial was filled with allyl galactoside 14 (57 mg, 0.26 mmol) and dibutyltinoxide (71 mg, 0.29 mmol), and the reagents were dried in vacuo. Dry PhMe/MeCN (5:1, 660l) was added,and the suspension in the sealed tube was exposed to microwave irradiation for 20 min at 150 C. The clear solution was allowed to cool to 50 C, and to the resulting suspension was added MeI (405l,6.5mmol)dropwise.The reaction was stirred for 48h at 50 C, after removal of the volatiles in vacuo and purification ofthe crude product by MPLC, the title compound was obtained as a pure product (40 mg, 65%). 1H NMR (400 MHz, MeOH-d4 )6.08-5.89(m,1H,CH 2CHCH 2 O-), 5.34 (dd, J 17.2, 1.8 Hz,1H, CH2 CHCH 2 O-), 5.17 (dd, J 10.4, 1.6 Hz, 1H,CH2 CHCH 2 O-), 4.85 (d, J 4.0 Hz, 1H, H1), 4.23 (ddt, J 13.0,5.3, 1.6 Hz, 1H, 1H, CH 2 CHCH2 O-), 4.13 (dd, J 3.3, 1.2 Hz,1H, H4), 4.04 (ddt, J 13.0, 6.1, 1.4 Hz, 1H, CH 2 CHCH2 O-),3.85 (dd, J 10.1, 3.9 Hz, 1H, H2), 3.82-3.77 (m, 1H, H5),3.76-3.63 (m, 2H, H6), 3.46 (s, 3H, CH 3 ), 3.42 (dd, J 10.1, 3.2Hz, 1H, H3). 13C NMR (101 MHz, MeOH-d4)135.65(CH 2CHCH 2 O-), 117.50 (CH 2 CHCH 2 O-), 99.37 (C1), 81.15(C3), 72.35 (C5), 69.38 (CH 2 CHCH 2 O-), 69.22 (C2), 66.91 (C4),62.74 (C6), 57.24 (CH 3 ). Transcripts of NMR spectra are shownin supplemental Figs. 6 and 7).
  • 26
  • [ 79-06-1 ]
  • [ 48149-72-0 ]
  • Poly(acrylamide-co-allyl α-D-galactoside), 7.5 percent allyl α-D-galactoside [ No CAS ]
  • 27
  • [ 79-06-1 ]
  • [ 48149-72-0 ]
  • [ 251365-50-1 ]
  • polymer, fluorescent; monomer(s): allyl α-D-galactopyranoside; acrylamide; allyl 6-O-(2-tert-butyl-2-methyl-1,3-benzodioxole-4-carbonyl-α-D-galactopyranoside [ No CAS ]
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  • [ 48149-72-0 ]
  • [ 168031-72-9 ]
  • [ 251365-50-1 ]
  • 29
  • [ 48149-72-0 ]
  • [ 3150-24-1 ]
  • allyl β-D-galactopyranosyl-(1->4)-α-D-galactopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Route a: 1-O-(2-propenyl)-alpha-D-galactose (II) Into 140 mL of allyl alcohol, 50.0 grams (278 mmol) of D-galactose (I) was added and sufficiently dissolved therein. To the solution, 0.5 mL of trifluoromethanesulfonic acid was gradually added under an ice-cooled condition. Then, the solution was reacted in an oil bath at 80 C. for 24 hours while stirring. At the stage where the reaction sufficiently proceeded, the reaction mixture was neutralized with 1.0 mL of triethylamine, concentrated in vacuo, and purified by silica gel flash chromatography (chloroform: methanol=6:1?5:1?4:1), to give a pale yellowish oily substance. The product was dissolved in hot ethanol and cooled to crystallize it, to give a colorless and needle crystal (yield 16.6 g, 75.5 mmol, recovery: 27.2%). m.p.;145-148 C. [alpha]D=+172.2 (c 0.97, CHCl3)
  • 31
  • [ 48149-72-0 ]
  • 4-MeOC6H4-X [ No CAS ]
  • [ 183954-75-8 ]
  • 32
  • [ 933-40-4 ]
  • [ 48149-72-0 ]
  • [ 282089-13-8 ]
  • 33
  • [ 100-39-0 ]
  • [ 48149-72-0 ]
  • [ 112344-80-6 ]
  • 34
  • [ 48149-72-0 ]
  • [ 80095-44-9 ]
  • Sulfuric acid mono-[(2R,3S,4R,5R,6S)-5-acetylamino-6-((2S,3R,4S,5S,6R)-2-allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl] ester [ No CAS ]
  • Sulfuric acid mono-[(2R,3S,4R,5R,6R)-5-acetylamino-6-((2R,3R,4S,5R,6S)-6-allyloxy-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethoxy)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl] ester [ No CAS ]
  • 35
  • [ 100-44-7 ]
  • [ 48149-72-0 ]
  • [ 61893-74-1 ]
 

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