[ CAS No. 113484-74-5 ] {[proInfo.proName]}

Name: 113484-74-5|Fmoc-Gly-OSu|95%
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Quality Control of [ 113484-74-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 113484-74-5 ]

SDS Specification

Alternatived Products of [ 113484-74-5 ]

Product Details of [ 113484-74-5 ]

CAS No. :	113484-74-5	MDL No. :	MFCD00065651
Formula :	C₂₁H₁₈N₂O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XZJJWLWTGNBBFM-UHFFFAOYSA-N
M.W :	394.38	Pubchem ID :	11246395
Synonyms :

Calculated chemistry of [ 113484-74-5 ]

Physicochemical Properties

Num. heavy atoms :	29
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.24
Num. rotatable bonds :	8
Num. H-bond acceptors :	6.0
Num. H-bond donors :	1.0
Molar Refractivity :	104.2
TPSA :	102.01 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.94
Log Po/w (XLOGP3) :	2.09
Log Po/w (WLOGP) :	1.75
Log Po/w (MLOGP) :	2.08
Log Po/w (SILICOS-IT) :	2.1
Consensus Log Po/w :	2.19

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.38
Solubility :	0.164 mg/ml ; 0.000417 mol/l
Class :	Soluble
Log S (Ali) :	-3.86
Solubility :	0.0542 mg/ml ; 0.000137 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.34
Solubility :	0.00178 mg/ml ; 0.00000452 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.9

Safety of [ 113484-74-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 113484-74-5 ]

* 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 [ 113484-74-5 ]
Downstream synthetic route of [ 113484-74-5 ]

[ 113484-74-5 ] Synthesis Path-Upstream 1~2

1
[ 56-40-6 ]
[ 113484-74-5 ]
[ 35665-38-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydrogencarbonate In tetrahydrofuran; 1,2-dimethoxyethane; water for 20 h;	For Fmoc-GlyGly-OH 1a, Glycine (75 mg, 1 mmol) and NaHCO₃ (100 mg, 1.2 mmol) were dissolved in H₂O (10 ml) and dimethoxyethane (DME) (5 ml). Fmoc-Gly-NHS solution in DME (5 ml, 1 mmol) was added. THF (2.5 ml) was added, the mixture was sonicated to make it homogeneous and stirred for 20 h. All volatiles were removed on a rotovap, the residue was treated with EtOAc and 5percent KHCO₃ solution in H₂O. Product was extracted four times with EtOAc, washed with brine at pH=3, dried (Na₂SO₄), concentrated and dried in vacuo. Yield 321 mg (90percent). MS: 775.0 [2M +2Na]⁺; 377.4 [M+Na]⁺; 355.1 [M+1]⁺.

Reference： [1] Patent: WO2015/21092, 2015, A1, . Location in patent: Page/Page column 37
[2] Journal of the American Chemical Society, 2003, vol. 125, # 45, p. 13680 - 13681

2
[ 6066-82-6 ]
[ 29022-11-5 ]
[ 113484-74-5 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 7, p. 999 - 1005
[2] Journal of the American Chemical Society, 2003, vol. 125, # 45, p. 13680 - 13681
[3] Tetrahedron, 2009, vol. 65, # 19, p. 3871 - 3877
[4] Patent: WO2015/21092, 2015, A1, . Location in patent: Page/Page column 36

[ 113484-74-5 ] Synthesis Path-Downstream 1~43

1
[ 6066-82-6 ]
[ 29022-11-5 ]
[ 113484-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0℃; for 20.58h;	For Fmoc-Gly-NHS, Fmoc-Gly-OH (891 mg, 3 mmol) and NHS (380 mg, 3.3 mmol) were stirred in THF (10 ml) at 0C for 5 mm and treated with a DCC solution (650 mg, 3.15 mmol) in THF (5 ml). The cooling bath was removed in 30 mm and the reactionmixture was stirred at 20C for 10 h. The solid DCU was filtered off, washed with THF and the solvent was removed on the rotovap. The product was weighed and dissolved in DME to make a 0.2 mlvi solution.

Reference： [1]Journal of Pharmaceutical Sciences,1994,vol. 83,p. 999 - 1005
[2]Journal of the American Chemical Society,2003,vol. 125,p. 13680 - 13681
[3]Tetrahedron,2009,vol. 65,p. 3871 - 3877
[4]Patent: WO2015/21092,2015,A1 .Location in patent: Page/Page column 36
[5]Angewandte Chemie - International Edition,2019,vol. 58,p. 1382 - 1386
Angew. Chem.,2019,vol. 131,p. 1396 - 1400,5
[6]Journal of Organic Chemistry,2020,vol. 85,p. 1484 - 1494

2
[ 14691-88-4 ]
[ 113484-74-5 ]
[ 155637-96-0 ]

Reference： [1]Journal of Pharmaceutical Sciences,1994,vol. 83,p. 999 - 1005

3
[ 159407-40-6 ]
[ 113484-74-5 ]
Wang resin-bound FmocPhe [ No CAS ]
pituitary adenylate cyclase-activating polypeptide (4-6) [ No CAS ]

Reference： [1]Organic letters,2001,vol. 3,p. 781 - 783

4
[ 142026-03-7 ]
[ 113484-74-5 ]
Wang resin-bound FmocPhe [ No CAS ]
Gly-D-allo-IlePhy [ No CAS ]

Reference： [1]Organic letters,2001,vol. 3,p. 781 - 783

5
[ 18523-48-3 ]
[ 113484-74-5 ]
Wang resin-bound FmocPro [ No CAS ]
FmocGlyGlyPro [ No CAS ]

Reference： [1]Organic letters,2001,vol. 3,p. 781 - 783

6
[ 40224-49-5 ]
[ 113484-74-5 ]
Wang resin-bound FmocPro [ No CAS ]
FmocGly-D-ValPro [ No CAS ]

Reference： [1]Organic letters,2001,vol. 3,p. 781 - 783

7
[ 113484-74-5 ]
[ 333366-27-1 ]
Wang resin-bound FmocPro [ No CAS ]
FmocGlyThrPro [ No CAS ]

Reference： [1]Organic letters,2001,vol. 3,p. 781 - 783

8
[ 338-69-2 ]
[ 113484-74-5 ]
Fmoc-Gly-D-Ala [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 13680 - 13681

9
[ 56-45-1 ]
[ 113484-74-5 ]
Fmoc-Gly-L-Ser [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 13680 - 13681

10
[ 72-19-5 ]
[ 113484-74-5 ]
Fmoc-Gly-L-Thr [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 13680 - 13681

11
[ 56-40-6 ]
[ 113484-74-5 ]
[ 35665-38-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydrogencarbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water; for 20h;	For Fmoc-GlyGly-OH 1a, Glycine (75 mg, 1 mmol) and NaHCO3 (100 mg, 1.2 mmol) were dissolved in H2O (10 ml) and dimethoxyethane (DME) (5 ml). <strong>[113484-74-5]Fmoc-Gly-NHS</strong> solution in DME (5 ml, 1 mmol) was added. THF (2.5 ml) was added, the mixture was sonicated to make it homogeneous and stirred for 20 h. All volatiles were removed on a rotovap, the residue was treated with EtOAc and 5% KHCO3 solution in H2O. Product was extracted four times with EtOAc, washed with brine at pH=3, dried (Na2SO4), concentrated and dried in vacuo. Yield 321 mg (90%). MS: 775.0 [2M +2Na]+; 377.4 [M+Na]+; 355.1 [M+1]+.

Reference： [1]Patent: WO2015/21092,2015,A1 .Location in patent: Page/Page column 37
[2]Journal of the American Chemical Society,2003,vol. 125,p. 13680 - 13681

12
1-[5-(3-amino-propylamino)-pentyl]-4-nitro-1H-pyrrole-2-carboxylic acid [ No CAS ]
[ 113484-74-5 ]
1-(5-{3-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-acetylamino]-propylamino}-pentyl)-4-nitro-1H-pyrrole-2-carboxylic acid [ No CAS ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 4171 - 4178

13
[ 914305-16-1 ]
[ 113484-74-5 ]
N-9-fluorenylmethoxycarbonyl-glycyl-trans-5-triphenylmethylthiomethyl-L-proline [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 4465 - 4468

14
[ 113484-74-5 ]
[ 863974-96-3 ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 4171 - 4178

15
[ 113484-74-5 ]
C₅₉H₈₂N₁₂O₁₀ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 4171 - 4178

16
[ 113484-74-5 ]
C₅₉H₈₀N₁₂O₁₂ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 4171 - 4178

17
[ 113484-74-5 ]
C₆₁H₈₄N₁₂O₁₁ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 4171 - 4178

18
C₃₁H₃₄N₂O₆ [ No CAS ]
[ 113484-74-5 ]
C₄₈H₄₇N₃O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The synthesis of Pro36-amide, utilizing 5-carboxyfluorescein as starting material, was carried out as follows (see FIG. 6C). The fluorescein derivative was condensed with 1,10-diaminodecane, forming an amide linkage at the less hindered carboxyl group. The terminal amine was reacted with the NHS ester of Fmoc-protected glycine. The Fmoc-protected amine was then deprotected and reacted with the NHS ester of alpha-bromophenylacetic acid. Nucleophilic displacement of the bromide with 3-mercaptopropanoic acid, followed by NHS activation of the acid and condensation with dioctadecylamine, gave the product.

Reference： [1]Patent: US2004/22843,2004,A1 .Location in patent: Page/Page column 27; Sheet 17/17

19
[ 4710-95-6 ]
[ 113484-74-5 ]
Fmoc-glycyl-mannosamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol; at 25℃; for 1h;	EXAMPLES EXAMPLE 1Fmoc-Glycyl-Mannosamine Synthesis and Purification[0185] The synthesis of Fmoc-glycyl-mannosamine (FGM) occurred in a non-aqueous solution involving two main compounds: D-Mannosamine HCl and Fmoc-Glycyl-OSu. Both materials were dry powders that were introduced into a system comprised of anhydrous methanol and sodium methoxide. The reaction was agitated at 250C for 1 h. The reaction was complete when the FGM concentration was greater than 15 mg/niL, determined by HPLC. The FGM synthesis was then rotovapped (20C) to about 8% of the initial volume. The chromatographic purification was performed using a Biotage prepacked silica column. The FGM solution was loaded onto the column in a 50:50 CHCl3: CH3 OH solution. The silica column was then washed with 18 column volumes (CV) of 3% CHCl3/ 97% CH3OH. Following the wash, FGM was eluted from the column using 14 CV of 15% CHCl3/ 85% CH3OH. Fractions containing material were pooled and then rotovapped (20C) to dryness and stored at 40C. The average recovery for this step from the repeat batches was 73.8%.[0186] Materials: The table below lists the materials used during the synthesis and <n="55"/>purification of Fmoc-Glycyl-Mannosamine (FGM). The first four reagents in the table were used during the synthesis of FGM. The last two reagents were used during the purification of FGM.[0187] The silica column was a Biotage 75M Silica column. The column volume for a 75M column was 0.5 L.; EXAMPLE 2I. Description of CMP-Glycyl-Sialic Acid and CMP-Sialic Acid-PEG Synthesis and Purification[0188] The production of CMP-Sialic Acid-PEG (PSC) was performed in two segments. First, a key intermediate, CMP-Glycyl-Sialic Acid (GSC), was synthesized, purified, and dried, and second, this intermediate was PEGylated, purified, and dried. A synthetic pathway for CMP-SA-PEG is shown below. <n="56"/>Synthetic Pathway for CMP-SA-PEG[0189] The first step in the synthesis of GSC was the reaction of mannosamine with <strong>[113484-74-5]Fmoc-Gly-OSu</strong> in methanol under basic conditions. The resulting Fmoc-glycyl- mannosamine was purified on a silica flash chromatography column. The purified Fmoc- glycyl-mannosamine then entered a two step enzymatic reaction.[0190] Fmoc-glycyl-mannosamine (FGM) was reacted with pyruvate to convert to Fmoc-glycyl-sialic acid. This reaction was catalyzed by a commercially available sialic acid aldolase. Fmoc-glycyl-sialic acid was then coupled to cytidine-5 '-monophosphate through a CMP-NAN synthetase catalyzed reaction with cytidine-5 '-triphosphate. The resulting product, CMP-Fmoc-glycyl-sialic acid, was purified on a Cl 8 reverse phase column.[0191] Finally, the Fmoc-group was removed from the CMP-Fmoc-glycyl-sialic acid by deprotection with dimethylamine, forming a precipitate. The resulting precipitate was filtered out of solution using a 0.2 mum membrane and discarded. The resulting solution was dried in a freeze dryer, yielding a white powder of CMP-glycyl-sialic acid (GSC). <n="57"/>[0192] Both CMP-SA-IOK PEG and CMP-SA-20K PEG were synthesized in a single step reaction of GSC with the appropriately sized mPEG-pNP. This reaction was performed in an 80:20 THF: H2O solution. Purification of the final product, CMP-SA- PEG (PSC), was performed by reverse phase chromatography. CMP-SA-IOK PEG was purified using a C8 reverse phase chromatography resin, and CMP-SA-IOK PEG was purified using a C4 reverse phase chromatography resin. The eluant from the reverse phase column was dried by lyophilization, yielding a white powder of purified CMP-SA- PEG.[0193] The process was scaled to produce approximately 1Og of the GSC intermediate. Approximately 5.5g of CMP-SA-20K was produced from 0.5g of GSC, while approximately 5.0g of CMP-SA-IOK PEG was produced from l.Og of GSC. The final CMP-SA-PEG products were approximately 90% pure with the major impurities being CMP and sialic acid-PEG, the primary breakdown products of CMP-SA-PEG.
	With sodium hydrogencarbonate; In ethanol; water; at 20℃;Inert atmosphere;	D-mannosamine is coupled with a slight excess of <strong>[113484-74-5]Fmoc-Gly-OSu</strong> in the presence of sodium hydrogen carbonate in a water and ethanol mixture at ambient temperature. An inert reactor is charged with D-mannosamine (50 g), <strong>[113484-74-5]Fmoc-glycine-O-succinimide</strong> (110 g), sodium bicarbonate (24 g), water (0.28 L) and ethanol (1 .1 L). The reaction mixture is stirred at 20C.The conversion is monitored by RP-HPLC and upon completion of reaction, toluene (2.4 L) and water (2.0 L) is added. The aqueous phase is washed with toluene (2x1 .5 L) and concentrated under reduced pressure (approximately 0.9 L distilled off at 40-50C). Sodium chloride (200 g) is added followed by 2-methyl-tetrahydrofurane (2.5 L)..The organic phase is dried with magnesium sulphate (100 g) and filtered. The filtercake is washed with 2-methyl-tetrahydrofurane (200 mL). The combined filtrate isconcentrated under reduced pressure at 40-50C to an oil or a foam.

Reference： [1]Patent: WO2007/56191,2007,A2 .Location in patent: Page/Page column 53-57
[2]Patent: WO2018/115309,2018,A1 .Location in patent: Page/Page column 2; 28

20
[ 2799-07-7 ]
[ 113484-74-5 ]
Fmoc-Gly-Cys(Trt)-OH [ No CAS ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 3871 - 3877

21
[ 113484-74-5 ]
[ 18836-50-5 ]
UDP-MurNAc-L-Ala-γ-D-Glu-L-Lys(Nε-Gly)-D-Ala-D-Ala [ No CAS ]

Reference： [1]Biochimie,2012,vol. 94,p. 985 - 990

22
[ 1391107-89-3 ]
[ 113484-74-5 ]
[ 1619923-24-8 ]

Yield	Reaction Conditions	Operation in experiment
83 mg		(R)-1-(3-(4-(N-(4-(4-(3-(2-(4-chlorophenyl)-1-isopropyl-5-methyl-4-(methylsulfonyl)-1H-pyrrol-3-yl)-5-fluorophenyl)piperazin-1-yl)phenyl)sulfamoyl)-2-(trifluoromethylsulfonyl)phenylamino)-4-(phenylthio)butyl)piperidin-4-yl 2-aminoacetate (1) A solution of BM-1197 (113 mg, 0.10 mmol) and <strong>[113484-74-5]Fmoc-Gly-OSu</strong> (43 mg, 0.11 mmol) in CH2Cl2 (2 mL) was stirred at room temperature for 1 hour until no BM-1197 was observed by TLC. The solution was concentrated in vacuo to provide crude precursor of 1 which was used for next step without purification. The resulting residue was dissolved in Aceonitrile (5 mL) and followed by addition of diethyl amine (0.2 mL, 2 mmol). The mixture was stirred at room temperature for overnight until no starting material was observed by TLC and concentrated in vacuo. The residue was purified by HPLC to give the product 1 (salt with TFA, 83 mg, yield 70% over two steps). The gradient ran from 60% of solvent A and 40% of solvent B to 20% of solvent A and 80% of solvent B in 40 min. MS (ESI) ink 1189.08 (M+H)+.

Reference： [1]Patent: US2014/199234,2014,A1 .Location in patent: Paragraph 0140

23
[ 113484-74-5 ]
C₃₄H₃₃N₃O₉ [ No CAS ]