[ CAS No. 139110-80-8 ] {[proInfo.proName]}

Name: 139110-80-8|(2R,3R,4S)-3-Acetamido-4-guanidino-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid|98%
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Quality Control of [ 139110-80-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 139110-80-8 ]

SDS Specification

Alternatived Products of [ 139110-80-8 ]

Product Details of [ 139110-80-8 ]

CAS No. :	139110-80-8	MDL No. :	MFCD00866966
Formula :	C₁₂H₂₀N₄O₇	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ARAIBEBZBOPLMB-UFGQHTETSA-N
M.W :	332.31	Pubchem ID :	60855
Synonyms :	GG 167;GR 121167X	Chemical Name :	(2R,3R,4S)-3-Acetamido-4-guanidino-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid

Calculated chemistry of [ 139110-80-8 ]

Physicochemical Properties

Num. heavy atoms :	23
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.58
Num. rotatable bonds :	8
Num. H-bond acceptors :	8.0
Num. H-bond donors :	8.0
Molar Refractivity :	75.65
TPSA :	198.22 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-10.44 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.07
Log Po/w (XLOGP3) :	-2.98
Log Po/w (WLOGP) :	-3.58
Log Po/w (MLOGP) :	-3.18
Log Po/w (SILICOS-IT) :	-3.12
Consensus Log Po/w :	-2.56

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	3.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	0.51
Solubility :	1060.0 mg/ml ; 3.2 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.62
Solubility :	79.4 mg/ml ; 0.239 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	1.64
Solubility :	14300.0 mg/ml ; 43.2 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.84

Safety of [ 139110-80-8 ]

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 [ 139110-80-8 ]

* 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 [ 139110-80-8 ]

[ 139110-80-8 ] Synthesis Path-Downstream 1~71

1
[ 1184-90-3 ]
sodium 5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate [ No CAS ]
[ 139110-80-8 ]

Reference： [1]Carbohydrate Research,1994,vol. 259,p. 301 - 305

2
[ 1184-90-3 ]
[ 130525-62-1 ]
[ 139110-80-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 1173 - 1180

3
[ 130525-62-1 ]
[ 66356-40-9 ]
[ 139110-80-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 1173 - 1180

4
[ 139110-80-8 ]
5-acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-L-arabino-hept-2-enonic acid [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 1181 - 1188

5
[ 149398-58-3 ]
[ 139110-80-8 ]

Yield	Reaction Conditions	Operation in experiment
69%		Step E: Preparation of zanamivirIn a reaction vessel, 7.3 g of the solid residue, from step D, was taken and to it 7.3 g of ammonium formate along with 140 ml ammonia added at 25C - 3O0C. The reaction mass was heated to 900C for 3 hrs. 0.7 g of charcoal was added to this reaction mass and content was stirred for about 1 hr. Then the mass was cooled to 20C - 25C and filtered. The filtrate was concentrated at 600C under vacuum to obtain residue in which 100 ml of methanol was added and stirred. The resulting solid was filtered and dried under vacuum to yield 5.0 g of the title compound (yield - 69%, HPLC purity - 85%).
69%		In a reaction vessel, 7.3 g of the solid residue, from step D, was taken and to it 7.3 g of ammonium formate along with 140 ml ammonia added at 25 C.-30 C. The reaction mass was heated to 90 C. for 3 hrs. 0.7 g of charcoal was added to this reaction mass and content was stirred for about 1 hr. Then the mass was cooled to 20 C.-25 C. and filtered. The filtrate was concentrated at 60 C. under vacuum to obtain residue in which 100 ml of methanol was added and stirred. The resulting solid was filtered and dried under vacuum to yield 5.0 g of the title compound (yield-69%, HPLC purity-85%).

Reference： [1]Patent: WO2010/61182,2010,A2 .Location in patent: Page/Page column 15
[2]Patent: US2011/257418,2011,A1 .Location in patent: Page/Page column 8
[3]Journal of the Chemical Society. Perkin transactions I,1995,p. 1173 - 1180

6
[ 913745-34-3 ]
[ 139110-80-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 5 - 20℃; for 0.5h;	Process for the preparation of 5-(acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-P-glycero-D-galacto-non-enonic acid (Formula I); Charged DBU (22.48 gm) in a vessel containing 5-acetamido-4-guanidino-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (as prepared in example-2) slowly at temp 5-10 C. Subsequently, the temperature was raised up to RT and maintained for 30 min. The reaction mass was washed with MDC and subsequently, acetone was added. The product thus obtained was isolated. The compound was filtered, washed with acetone and dried under reduced pressure at 50 C. The yield was 6.7 g (61.3%). HPLC Purity-99.5%
61.3%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 5 - 25℃; for 0.5h;Product distribution / selectivity;	Example-6: Process for the preparation of 5-(acetylamino)-4- [(aminoiminomethyl)aminol-2,6-anhvdro-3,4,5-trideoxy-D-glycero-D-galacto-non- enonic acid (Formula I) Charged DBU (22.48gm) in a vessel containing 5-acetamido-4-guanidino-6- (l,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (as prepared in example- 2) slowly at temp 5-10 C. Subsequently, the temperature was raised up to RT and maintained for 30 min. The reaction mass was washed with MDC and subsequently, acetone was added. The product thus obtained was isolated. The compound was filtered, washed with acetone and dried under reduced pressure at 50 C.The yield was 6.7 g (61.3 %). HPLC Purity - 99.5%

Reference： [1]Patent: US2014/73804,2014,A1 .Location in patent: Paragraph 0053; 0054
[2]Patent: WO2012/114350,2012,A1 .Location in patent: Page/Page column 15-16
[3]Organic Preparations and Procedures International,1995,vol. 27,p. 637 - 644

7
C₁₇H₃₅BrO [ No CAS ]
[ 139110-80-8 ]
C₂₉H₅₄N₄O₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4851 - 4854

8
[ 126614-26-4 ]
[ 139110-80-8 ]
C₃₁H₅₈N₄O₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4851 - 4854

9
[ 139110-80-8 ]
[ 343248-28-2 ]
C₃₂H₆₀N₄O₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4851 - 4854

10
[ 20298-35-5 ]
[ 139110-80-8 ]

Reference： [1]Organic Preparations and Procedures International,1995,vol. 27,p. 637 - 644

11
[ 73960-72-2 ]
[ 139110-80-8 ]

Reference： [1]Organic Preparations and Procedures International,1995,vol. 27,p. 637 - 644

12
[ 132883-18-2 ]
[ 139110-80-8 ]

Reference： [1]Organic Preparations and Procedures International,1995,vol. 27,p. 637 - 644

13
[ 80973-54-2 ]
[ 139110-80-8 ]

Reference： [1]Organic Preparations and Procedures International,1995,vol. 27,p. 637 - 644

14
[ 78850-37-0 ]
[ 139110-80-8 ]

Reference： [1]Organic Preparations and Procedures International,1995,vol. 27,p. 637 - 644
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 1644 - 1647
[3]Journal of the American Chemical Society,2013,vol. 135,p. 13254 - 13257

15
[ 130525-58-5 ]
[ 139110-80-8 ]

Reference： [1]Organic Preparations and Procedures International,1995,vol. 27,p. 637 - 644
[2]Patent: US2011/257418,2011,A1
[3]Angewandte Chemie - International Edition,2012,vol. 51,p. 1644 - 1647
[4]Patent: WO2012/114350,2012,A1
[5]Journal of the American Chemical Society,2013,vol. 135,p. 13254 - 13257
[6]Patent: US2014/73804,2014,A1

16
[ 6931-68-6 ]
[ 139110-80-8 ]

Reference： [1]Organic Preparations and Procedures International,1995,vol. 27,p. 637 - 644

17
[ 139110-70-6 ]
[ 139110-80-8 ]

Reference： [1]Organic Preparations and Procedures International,1995,vol. 27,p. 637 - 644
[2]Patent: US2011/257418,2011,A1
[3]Angewandte Chemie - International Edition,2012,vol. 51,p. 1644 - 1647
[4]Journal of the American Chemical Society,2013,vol. 135,p. 13254 - 13257

Yield	Reaction Conditions	Operation in experiment
		cellulose acetate and polyethylene glycol 400 are added to acetone and mixed thoroughly to form a polymer solution.

Yield	Reaction Conditions	Operation in experiment
	With pyrographite; In water; isopropyl alcohol; at 20 - 90℃;Purification / work up;	Step F: Purification of <strong>[139110-80-8]zanamivir</strong>Crude <strong>[139110-80-8]zanamivir</strong> (5 g), from earlier step, was stirred with 50 ml of water and heated to 900C to get suspension. To it 4 g charcoal was added and filtered hot through hyflo to get a clear solution. To the clear filtrate 15 ml of isopropyl alcohol was added dropwise. The solid thus obtained was filtered, washed with isopropyl alcohol and dried under vacuum at 60C to obtain 2.5 g of pure <strong>[139110-80-8]zanamivir</strong> (HPLC purity - 99.5%).

20
amantadine-C₇-Neu₅Ac [ No CAS ]
[ 139110-80-8 ]
C₃₁H₄₈N₆O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 8Preparation of Compound [amantadine-C7-Neu5Ac-Ci2 20N4Oy] having the following structural formula:The compound obtained from the previous phase (amantadine-C7-Neu5Ac) is dissolved in 10 ml of distilled water and 2.69 g of C12H20N4O7 {CAS[ 139110-80-8] ; M .W. 332.30} are added . Incubate the sample during 2 hours at 60C under stirring . Add 1.37 g of sodium cyanoborohydride (NaBH3CN) . Incubate the sample at 60 C under stirring overnight.Centrifugate and eliminate the supernatant. Wash at least once with 30 and 50 ml of distilled water. Centrifugate again and eliminate the supernatant. Add 50 ml of the solvent mixture chloroform : methanol : NH4OH 15 M (60 : 35 : 8 ; V/V/V) . Incubate the sample during 1 hour at room temperature under stirring . Centrifugate, dry the supranatant into a rotating desiccator. Place the dried sample in a minimum volume of water. Lyophilize and store the sa m ple in freezer at -20 C.

Reference： [1]Patent: WO2011/64303,2011,A1 .Location in patent: Page/Page column 48-49

21
rimantadine-C₇-Neu₅Ac [ No CAS ]
[ 139110-80-8 ]
C₃₃H₅₂N₆O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 13Preparation of Compound [rimantadine-C7-Neu5Ac-Ci2H20N4O7] having the following structural formula:The compound obtained from the previous phase (rimantadine-C7-Neu5Ac) is dissolved in 10 ml of distilled water and 2.69 g of C12H20N4O7 {CAS[ 139110-80-8] ; M .W. 332.30} are added . Incubate the sample during 2 hours a 60 C under stirring . Add 1.37 g of sodium cyanoborohydride(NaBH3CN) . Incubate the sample at 60C under stirring overnight.Centrifugate and eliminate the supernatant. Wash at least once with 30 and 50 ml of distilled water. Centrifugate again and eliminate the supernatant. Add 50 ml of the solvent mixture Chloroform : Methanol : NH4OH 15 M (60 : 35 : 8 ; V/V/V) . Incubate the sample during 1 hour at room temperature under stirring . Centrifugate, dry the supernatant into a rotating desiccator. Place the dried sample in a minimum volume of water. Lyophilize and store the sample in freezer at -20 C.

Reference： [1]Patent: WO2011/64303,2011,A1 .Location in patent: Page/Page column 52

22
[ 1228216-82-7 ]
[ 139110-80-8 ]

Reference： [1]Patent: US2011/257418,2011,A1

23
[ 1372800-41-3 ]
[ 139110-80-8 ]