[ CAS No. 17364-16-8 ] {[proInfo.proName]}

Name: 17364-16-8|(R)-2-Hydroxy-3-(palmitoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate|98%
Brand: Ambeed
SKU: A865426
Rating: 96 (29 reviews)

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2D 3D

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Quality Control of [ 17364-16-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17364-16-8 ]

SDS Specification

Alternatived Products of [ 17364-16-8 ]

Product Details of [ 17364-16-8 ]

CAS No. :	17364-16-8	MDL No. :	MFCD00036904
Formula :	C₂₄H₅₀NO₇P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ASWBNKHCZGQVJV-HSZRJFAPSA-N
M.W :	495.63	Pubchem ID :	460602
Synonyms :	lyso-PPC;1-Palmitoyl-sn-glycero-3-phosphorylcholine	Chemical Name :	(R)-2-Hydroxy-3-(palmitoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate

Calculated chemistry of [ 17364-16-8 ]

Physicochemical Properties

Num. heavy atoms :	33
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.96
Num. rotatable bonds :	24
Num. H-bond acceptors :	7.0
Num. H-bond donors :	1.0
Molar Refractivity :	132.77
TPSA :	114.93 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.76
Log Po/w (XLOGP3) :	5.64
Log Po/w (WLOGP) :	5.65
Log Po/w (MLOGP) :	-1.13
Log Po/w (SILICOS-IT) :	5.18
Consensus Log Po/w :	3.22

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.88
Solubility :	0.0065 mg/ml ; 0.0000131 mol/l
Class :	Moderately soluble
Log S (Ali) :	-7.82
Solubility :	0.00000755 mg/ml ; 0.0000000152 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-6.68
Solubility :	0.000103 mg/ml ; 0.000000207 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	5.48

Safety of [ 17364-16-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 17364-16-8 ]

* 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 [ 17364-16-8 ]

[ 17364-16-8 ] Synthesis Path-Downstream 1~88

1
[ 623-65-4 ]
[ 17364-16-8 ]
[ 63-89-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1991,p. 926 - 938

2
[ 7501-44-2 ]
[ 645-84-1 ]
[ 17364-16-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1991,p. 926 - 938

3
[ 17364-16-8 ]
1-Imidazol-1-yl-21-[4-((1E,3E,5E)-6-phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosan-1-one [ No CAS ]
[ 128368-78-5 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1990,p. 31 - 32

4
[ 17364-16-8 ]
[ 128368-79-6 ]
[ 128368-78-5 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 1459 - 1472

5
[ 17364-16-8 ]
[ 116405-88-0 ]
C₄₁H₈₀NO₁₀P [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7463 - 7469

6
[ 17364-16-8 ]
[ 108-24-7 ]
[ 79512-78-0 ]

Reference： [1]Journal of the American Oil Chemists' Society,2008,vol. 85,p. 1005 - 1011
[2]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 4425 - 4435
[3]Chemistry and Physics of Lipids,2007,vol. 147,p. 113 - 118

7
[ 17364-18-0 ]
[ 17364-16-8 ]

Reference： [1]Synthetic Communications,1993,vol. 23,p. 2135 - 2138

8
[ 17364-16-8 ]
1,10-decanedioic acid mono-2-iodo-4-<(trifluoromethyl)-3H-diazirin-3-yl>benzyl ester [ No CAS ]
1-O-hexadecanoyl-2-O-<9-<<<2-iodo-4-<(trifluoromethyl)-3H-diazirin-3-yl>benzyl>oxy>carbonyl>nonanoyl>-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 3084 - 3095

9
[ 90677-38-6 ]
[ 17364-16-8 ]
1-palmitoyl-2-(8-methoxyoctanoyl)-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7382 - 7390

10
[ 92169-28-3 ]
[ 17364-16-8 ]
1-palmitoyl-2-(12-methoxydodecanoyl)-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7382 - 7390

11
[ 693-23-2 ]
[ 17364-16-8 ]
1-palmitoyl-2-(11-carboxyundecanoyl)-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7382 - 7390

12
[ 17364-16-8 ]
[ 77744-42-4 ]
[ 183145-38-2 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7382 - 7390

13
[ 17364-16-8 ]
[ 203244-15-9 ]
1-palmitoyl-2-(2,4,12,14-tetraenepalmitoyl)phosphatocholine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 11327 - 11328
[2]Journal of the American Chemical Society,1998,vol. 120,p. 2322 - 2329

14
[ 17364-16-8 ]
[ 55726-27-7 ]
1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

15
[ 29603-38-1 ]
[ 17364-16-8 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

16
[ 59404-48-7 ]
[ 17364-16-8 ]
1-palmitoyl-2-((E,E)-2,4-hexadecadienoyl)-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 15397 - 15414

17
[ 17364-16-8 ]
[ 127660-38-2 ]
L-α-palmitoyl-2-[1-11C]butyryl-sn-glycero-3-phosphorylcholine [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1995,vol. 5,p. 97 - 112

19
[ 17364-16-8 ]
4-[2-iodo-4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-butyric acid [ No CAS ]
C₃₆H₅₈F₃IN₃O₉P [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 6737 - 6741

20
[ 17364-16-8 ]
4-[2-tributylstannanyl-4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-butyric acid [ No CAS ]
C₃₆H₅₈F₃IN₃O₉P [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 6737 - 6741

21
[ 63-89-8 ]
[ 17364-16-8 ]
[ 57-10-3 ]

Reference： [1]Angewandte Chemie - International Edition in English,2000,vol. 39,p. X3059-3062

22
[ 63-89-8 ]
[ 17364-16-8 ]

Reference： [1]PLoS ONE,2016,vol. 11
[2]Journal of Materials Chemistry,2000,vol. 10,p. 1047 - 1059

23
[ 17364-16-8 ]
[ 125943-49-9 ]
[ 111363-74-7 ]

Reference： [1]Journal of Materials Chemistry,2000,vol. 10,p. 1047 - 1059

24
[ 14912-92-6 ]
(R)-glycidyl phosphocholine [ No CAS ]
[ 17364-16-8 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 194 - 199

25
[ 17364-16-8 ]
[ 254968-74-6 ]
[ 423756-19-8 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1678 - 1685

26
[ 17364-16-8 ]
C₃₈H₄₆F₈N₈O₅ [ No CAS ]
[ 423756-19-8 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1678 - 1685

27
[ 108-30-5 ]
[ 17364-16-8 ]
1-palmitoyl-2-succinoyl-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 3749 - 3761
[2]Chemistry and Physics of Lipids,2003,vol. 126,p. 29 - 38

28
[ 591-80-0 ]
[ 17364-16-8 ]
1-palmitoyl-2-(4-pentenoyl)-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 3749 - 3761

29
[ 935-13-7 ]
[ 17364-16-8 ]
[ 540742-94-7 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 3749 - 3761

30
[ 17364-16-8 ]
[ 543692-36-0 ]
[ 543692-38-2 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 3749 - 3761

31
[ 108-55-4 ]
[ 17364-16-8 ]
1-palmitoyl-2-glutaroyl-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Chemistry and Physics of Lipids,2003,vol. 126,p. 29 - 38

32
[ 17364-16-8 ]
[ 685888-15-7 ]
1-palmitoyl-2-{11-[4-(4-methylbenzoyl)phenyl]-undec-5-enoyl}-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 2693 - 2702

33
[ 17364-16-8 ]
[ 685887-87-0 ]
1-palmitoyl-2-{11-[4-(4-methylbenzoyl)-phenyl]-undecyl-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 2693 - 2702

34
[ 605680-01-1 ]
[ 17364-16-8 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1691 - 1698
[2]Tetrahedron Letters,2004,vol. 45,p. 7371 - 7373

35
[ 50530-12-6 ]
[ 17364-16-8 ]
C₃₄H₆₇BrNO₈P [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 2941 - 2944

36
[ 17364-16-8 ]
[ 128917-74-8 ]
[ 852385-14-9 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 2941 - 2944
[2]Journal of Organic Chemistry,2008,vol. 73,p. 6053 - 6058
[3]Journal of the American Chemical Society,2008,vol. 130,p. 17274 - 17275

37
[ 17364-16-8 ]
(4-methyl-7-mercaptocoumarin-7-yl)-10-decanoic acid [ No CAS ]
C₄₄H₇₄NO₁₀PS [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 2941 - 2944

38
[ 6753-55-5 ]
[ 17364-16-8 ]

Reference： [1]Chemistry and Physics of Lipids,2005,vol. 133,p. 1 - 15

39
[ 865302-36-9 ]
[ 17364-16-8 ]
[ 865302-38-1 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 3933 - 3935

40
[ 862251-69-2 ]
[ 17364-16-8 ]
1-palmitoyl-2-[(5R,6R,7E,12S)-5,6-epoxyisoprostane A₂]-sn-glycero-3-phosphorylcholine [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 8435 - 8438
[2]Angewandte Chemie - International Edition,2005,vol. 44,p. 3481 - 3484

41
[ 871581-80-5 ]
[ 17364-16-8 ]
14,15-epoxyisoprostane A₂ phosphorylcholine [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 8435 - 8438
[2]Heterocycles,2008,vol. 76,p. 1181 - 1189

42
[ 862251-75-0 ]
[ 17364-16-8 ]
C₄₄H₇₆NO₁₀P [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 8435 - 8438

43
[ 60-33-3 ]
[ 17364-16-8 ]
[ 6931-84-6 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 3481 - 3484

44
[ 2082-59-9 ]
[ 17364-16-8 ]
[ 120029-77-8 ]

Reference： [1]Chemistry and Physics of Lipids,2007,vol. 147,p. 113 - 118

45
[ 2051-49-2 ]
[ 17364-16-8 ]
[ 77444-40-7 ]

Reference： [1]Chemistry and Physics of Lipids,2007,vol. 147,p. 113 - 118
[2]Journal of the American Oil Chemists' Society,2008,vol. 85,p. 1005 - 1011

46
[ 1680-36-0 ]
[ 17364-16-8 ]
1-O-hexadecanoyl-2-O-nonanoyl-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Chemistry and Physics of Lipids,2007,vol. 147,p. 113 - 118
[2]Journal of the American Oil Chemists' Society,2008,vol. 85,p. 1005 - 1011

47
[ 28319-77-9 ]
[ 112-67-4 ]
[ 17364-16-8 ]

Yield	Reaction Conditions	Operation in experiment
31%		General procedure: This compound was prepared as in the literature with some modifications.4 NMR spectra of this compound and of regioisomers can be found elsewhere.5 Migration in compound 7 has been reported when silica gel chromatography was used for purification,6 and sufficient isomeric purity was concluded from 1H- and 13C-NMR in our synthetic protocol. A 100 mL one-neck round-bottom flask equipped with a reflux condenser, was consecutively charged with 2.00 g (8.3 mmol, 1 eq) GPC (6), 2.20 g (8.83 mmol, 1.1 eq) dibutyltin oxide and 80 mL iPrOH. The flask was placed in a pre-heated oil-bath (~100 C) and it was stirred for 1 h at this temperature. It was cooled to rt, after which 1.3 mL (9.38 mmol, 1.1 eq) Et3N and 2.8 mL (9.2 mmol, 1.1 eq) palmitoyl chloride were added and it was stirred at rt overnight. Subsequently, the mixture was transferred into a separation funnel containing 80 mL H2O and the aqueous layer was washed with pentane (3x80 mL). The aqueous layer was then concentrated in vacuo and the crude product was purified via flash column chromatography (19 g SiO2 gel, 11.8x2.3 cm, 15 mL frac., frac. 6-27 pooled). Yield= 1.28 g (2.58 mmol, 31 %), colorless solid C24H50NO7P [495.63 g·mol-1] Rf= 0.25 (CH2Cl2/MeOH/H2O= 65/25/4, KMnO4) 1H-NMR (300 MHz, MeOD-d4): delta= 4.36-4.24 (m, 2H), 4.24-3.84 (m, 5H), 3.72-3.62 (m, 2H), 3.22 (s, 9H), 2.36 (t, J= 7.5 Hz, 2H), 1.71-1.53 (m, 2H), 1.43-1.19 (m, 24H), 0.90 (t, J= 6.7 Hz, 3H). 13C-NMR (75 MHz, MeOD-d4): delta= 175.3, 69.7, 67.9, 67.5, 66.2, 60.5, 54.7, 34.9, 33.1, 31.0-30.0 (m), 26.0, 23.7, 14.5. Missing signals due to overlap.

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2974 - 2978
[2]Australian Journal of Chemistry,2013,vol. 66,p. 354 - 361
[3]Chemistry and Physics of Lipids,2007,vol. 147,p. 113 - 118
[4]Journal of the American Oil Chemists' Society,2008,vol. 85,p. 1005 - 1011
[5]Tetrahedron Letters,2017,vol. 58,p. 2651 - 2653

48
[ 106-31-0 ]
[ 17364-16-8 ]
[ 77444-39-4 ]

Reference： [1]Chemistry and Physics of Lipids,2007,vol. 147,p. 113 - 118
[2]Journal of the American Oil Chemists' Society,2008,vol. 85,p. 1005 - 1011

49
[ 17364-16-8 ]
[ 123-62-6 ]
[ 77444-38-3 ]

Reference： [1]Chemistry and Physics of Lipids,2007,vol. 147,p. 113 - 118
[2]Journal of the American Oil Chemists' Society,2008,vol. 85,p. 1005 - 1011

50
[ 951241-47-7 ]
[ 17364-16-8 ]
2-(14,15-dehydro-5,6-epoxyisoprostane A₂)phosphorylcholine [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 3535 - 3538

51
C₁₈H₂₃N₂O₂BF₂ [ No CAS ]
[ 17364-16-8 ]
C₄₂H₇₁N₃O₈PBF₂ [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 78 - 83

52
7-(5,5-difluoro-1,3,7,9-tetramethyl-5H-44,54-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-10-yl)heptanoic acid [ No CAS ]
[ 17364-16-8 ]
C₄₄H₇₅N₃O₈PBF₂ [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 78 - 83

53
9-(Me₄-BODIPY-8)nonanoic acid [ No CAS ]
[ 17364-16-8 ]
C₄₆H₇₉N₃O₈PBF₂ [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2006,vol. 32,p. 78 - 83

54
hexadecanoic acid 3-acetoxy-2-(tetrahydro-pyran-2-yloxy)-propyl ester [ No CAS ]
[ 17364-16-8 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1691 - 1698

55
[ 932378-54-6 ]
[ 17364-16-8 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1691 - 1698

56
[ 932378-52-4 ]
[ 17364-16-8 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1691 - 1698
[2]Journal of Organic Chemistry,2007,vol. 72,p. 1691 - 1698

57
[ 57984-42-6 ]
[ 17364-16-8 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1691 - 1698
[2]Journal of Organic Chemistry,2007,vol. 72,p. 1691 - 1698

58
[ 605680-00-0 ]
[ 17364-16-8 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1691 - 1698
[2]Tetrahedron Letters,2004,vol. 45,p. 7371 - 7373

59
Hexadecanoic acid (R)-3-(2-oxo-2λ⁵-[1,3,2]dioxaphospholan-2-yloxy)-2-(tetrahydro-pyran-2-yloxy)-propyl ester [ No CAS ]
[ 17364-16-8 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1691 - 1698
[2]Tetrahedron Letters,2004,vol. 45,p. 7371 - 7373

60
[ 17364-16-8 ]
[ 250142-34-8 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 2941 - 2944

61
[ 17364-16-8 ]
1-palmitoyl-2-[12'-(PROXYL-3"-carbamoyl)aminolauroyl]-sn-3-glycero-phosphocholine [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 2941 - 2944

62
[ 17364-16-8 ]
1-palmitoyl-2-[12'-(2"-naphthylacetyl)aminolauroyl]-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 2941 - 2944

63
[ 17364-16-8 ]
C₆₄H₁₂₃N₆O₁₅P [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 2941 - 2944

64
[ 786704-18-5 ]
[ 17364-16-8 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 7371 - 7373

65
[ 786704-19-6 ]
[ 17364-16-8 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 7371 - 7373

66
[ 17364-16-8 ]
2-(4-oxobutyryl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 3749 - 3761

67
[ 17364-16-8 ]
[ 540742-96-9 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 3749 - 3761

68
[ 17364-16-8 ]
2-(6-carboxy-4-oxohex-5-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 3749 - 3761

69
[ 17364-16-8 ]
1-O-palmitoyl-2-O-[12-[N-(4-azido-2,3,5,6-tetrafluorobenzoyl)]amidododecanoyl]-sn-glycero-3-phosphochate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1678 - 1685
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 1678 - 1685

70
[ 55357-38-5 ]
[ 17364-16-8 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 194 - 199

71
[ 17618-07-4 ]
[ 17364-16-8 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

72
[ 18282-29-6 ]
[ 17364-16-8 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

73
[ 57-10-3 ]
[ 17364-16-8 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

74
[ 172794-56-8 ]
[ 17364-16-8 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

75
1-palmitoyl-2,5,6-tribenzyl-3,4-isopropylidene-D-mannitol [ No CAS ]
[ 17364-16-8 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

76
1-palmitoyl-2,5,6-tribenzyl-D-mannitol [ No CAS ]
[ 17364-16-8 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 451 - 458

77
[ 17364-16-8 ]
[ 116405-89-1 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7463 - 7469

78
[ 17364-16-8 ]
[ 116405-87-9 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7463 - 7469

79
[ 623-65-4 ]
[ 17364-16-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 39 percent / 4-(dimethylamino)pyridine / CHCl₃ / Ambient temperature 2: 88 percent / CaCl₂ / ethanol; diethyl ether / phospholipase A₂ in the form of crude rattle snake venom (Crotalus admanteus)

Reference： [1]Regen, Steven L.; Singh, Alok; Oehme, Guenter; Singh, Maninder [Journal of the American Chemical Society, 1982, vol. 104, # 3, p. 791 - 795]

80
[ 408-35-5 ]
[ 17364-16-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1991,p. 926 - 938

81
[ 112-67-4 ]
ent-17-methyl-morphinan-3-ol [ No CAS ]
[ 17364-16-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1991,p. 926 - 938

82
[ 1577-22-6 ]
[ 17364-16-8 ]
1-hexadecanoyl-2-(5'-hexenoyl)-sn-3-glycerophosphcholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1,3-Dicyclohexylurea; In dichloromethane; at 20℃; for 96h;	A mixture of 1-hexadecanoyl-sn-3-glycerophosphocholine (compound I, FIG. 2), L-alpha-palmitoyl-lysophosphatidylcholine (3 grams), 5-hexenoic acid (1.2 ml), 1,3-dicyclohexylcarbodiamide (DCC, 4.05 grams) and N,N-dimethylaminopyridine (DMP, 1.6 grams) in dichloromethane (100 ml, freshly distilled from phosphorus pentoxide) was thoroughly stirred for 4 days at room temperature. The mixture was then chromatographed on silica gel 60 (40 grams) and the product, 1-hexadecanoyl-2-(5'-hexenoyl)-sn-3-glycerophosphocholine (2.8 grams, compound II, FIG. 2) was eluted with a mixture of 25:75 chloroform:methanol. The eluent was dissolved in 30% hydrogen peroxide:formic acid (4:15) and the solution was stirred overnight at room temperature. Water (50 ml) were added, the product was extracted with 2:1 chloroform:methanol (100 ml) and the organic phase was washed with water. The solvent was evaporated under reduced pressure, the residue was dissolved in methanol (15 ml) and 10% ammonia solution (5 ml) and the solution was stirred at room temperature for 6 hours. The crude 1-hexadecanoyl-2-(5',6'-dihydroxy)-hexanoyl-sn-3-glycerophosphocholine (compound III, FIG. 2) (structure confirmed by NMR and mass spectrometry) was further reacted without puirofocation. 80% phosphoric acid (3 ml) and sodium metaperiodate (1 gram) were added to the solution and the mixture was stirred at room temperature for overnight, and was thereafter extracted with a mixture of 2:1 chloroform:methanol. The product was purified by chromatography on silica gel 60 (20 grams), using a mixture of 25:75 chloroform:methanol as eluent. 850 mg of 1-hexadecanoyl-2-(5'-oxopentanoyl)-sn-3-glycerophosphocholine (POVPC, compound IV, FIG. 2) were obatined, exhibiting chromatographic mobility of lecithin on TLC, and positive dinitrophenyl hydrazine reaction. The structure was assessed by NMR and mass spectrometry. [0210] Alternatively: the ethylenic group was converted to an aldehyde by ozonization and catalytic hydrogenation with palladium calcium carbonate.

Reference： [1]Patent: US2003/225035,2003,A1 .Location in patent: Page 17

83
[ 112-67-4 ]
[ 17364-16-8 ]

Yield	Reaction Conditions	Operation in experiment
98%		Example 8 Palmitoyl-lyso-PC A suspension of 2.5 g GPC (I), 2.5 g DBTO (1 eq), and 35 ml methanol was stirred at reflux until a clear solution was obtained (1.5 hr.), after which the methanol was evaporated to a residue of 5 ml. 25 ml of WA was added, the mixture was concentrated again at ordinary pressure to a residual volume of 5 ml, and 25 ml of WA was added. 1.6 ml TEA (1.2 eq) and 3.2 g palmitoyl chloride (1.2 eq) were added by dropping at 25 C. The conversion (31PNIvIR) at the end of the dropping was >98%. 25 ml of heptane was added to the suspension and, after cooling to 0 C. and holding at 0 C. for 30 minutes, 5.2 g of solid was obtained by filtration. The solid was recrystallized in heptanol/WA, giving 4.7 g of high-purity product after drying (a yield of 98%).
92%		A suspension of 2.5 g of GPC (I) (1 eq.), 0.5 g of DBTO (0.2 eq), and 35 ml of methanol was stirred at reflux for 1 hr, to produce a clear solution from which the methanol was evaporated to give a residual volume of 5 ml. 25 ml of IPA was added and the solution was evaporated to a volume of 5 ml, another 25 ml of IPA being added to the residue. 1.6 ml of TEA (1.2 eq) was dropped in, the temperature was raised to 40 C., and 3.2 g (1.2 eq) of palmitoyl chloride was dropped in, the reaction being sampled at the end of the dropping. Another 0.8 eq. of TEA was added and 0.8 eq. of palmitoyl chloride was dropped in. The conversions (31PNMR) were 90% after the first step and >99% after the second step of dropping (2 eq. total). 25 ml of heptane was added to the solution, which was then cooled to 0 C. and filtered. This produced 7.6 g of wet product which was recrystallized by a mixture of heptanol and IPA, resulting in 4.4 g of lyso-PC after drying (a yield of 92%).
		Example 6 Palmitoyl-lyso-PC A suspension of 2.5 g of GPC (I) and 2.5 g of DBTO in 125 ml of IPA was stirred at reflux temperature for 1 hr. After the temperature had been raised to 40 C., 1.62 ml of TEA and 3.24 g of palmitoyl chloride were dropped in. The conversion to palmitoyl-lyso-PC was 88% (31P NMR).

Reference： [1]Patent: US2006/79703,2006,A1 .Location in patent: Page/Page column 4
[2]Patent: US2006/79703,2006,A1 .Location in patent: Page/Page column 4
[3]Patent: US2006/79703,2006,A1 .Location in patent: Page/Page column 4

84
[ 112-67-4 ]
[ 17364-16-8 ]
1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 1 Palmitoyl-lyso-PC A suspension of 2.5 g of GPC (I) (1 eq.), 2.5 g of DBTO (1 eq) and 35 ml of methanol was stirred at reflux to form a clear solution (1.5 hrs.) and the methanol was evaporated to leave a residue of 5 ml. 25 ml of WA was added, the mixture was concentrated again at ordinary pressure to give a residual volume of 5 ml, and 25 ml of IPA was added. 1.6 ml of TEA (1.2 eq) and 3.2 g of palmitoyl chloride (1.2 eq) were dropped in at 25 C. At the end of the dropping, the conversion (31P-NMR) was >99%, and the ratio between the two lyso-PCs was 1:9 in favour of the compound acylated at position sn-1.
		A suspension of 0.5 g GPC (I), 0.5 g DBTO (1 eq), and 10 ml methanol was stirred at reflux until a clear solution was obtained (1 hr.) and the methanol was evaporated to a residual volume of 1 ml. 5 ml of IPA was added and the solution was concentrated again at ordinary pressure to a residual volume of 1 ml, after which 5 ml of WA was added. At 25 C., 0.220 g of DMAP (1.2 eq) was added and 0.64 g of palmitoyl chloride (1.2 eq) was dropped in. At the end of the dropping, the conversion (31PNMR) was 86%, and the ratio between the two forms of lyso-PC was 1:50 in favour of the compound acylated at position sn-1.
		2.5 g of GPC (I), 3.5 g of DOTO (1 eq), and 35 ml of methanol were placed in a three-necked flask under a nitrogen flow, and were stirred at reflux temperature for two hours; the result was a white suspension to which 24 ml of IPA was added and then evaporated at ordinary pressure. IPA (50 ml) was added to the residue and the suspension was left to cool to 25 C. When the temperature was stabilized, 1.62 ml of TEA (1.2 eq) and 3.24 g of palmitoyl chloride (1.2 eq) were dropped in. The conversion (31PNMR) was >99%, and the ratio between the two lyso-PCs was 1:9 in favour of the compound acylated at position sn-1.

Reference： [1]Patent: US2006/79703,2006,A1 .Location in patent: Page/Page column 3
[2]Patent: US2006/79703,2006,A1 .Location in patent: Page/Page column 4
[3]Patent: US2006/79703,2006,A1 .Location in patent: Page/Page column 4

85
[ 1039749-80-8 ]
[ 17364-16-8 ]
[ 1039749-81-9 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6053 - 6058

86
[ 2777-65-3 ]
[ 17364-16-8 ]
[ 923579-61-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6053 - 6058

87
[ 2082-76-0 ]
[ 17364-16-8 ]
[ 106268-87-5 ]

Reference： [1]Journal of the American Oil Chemists' Society,2008,vol. 85,p. 1005 - 1011

88
[ 6931-84-6 ]
[ 17364-16-8 ]

Reference： [1]Bioorganic Chemistry,2009,vol. 37,p. 202 - 210

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